


Light My Fire

by smolandgrumpy



Category: Supernatural
Genre: Angst, Business AU, CEO!Dean Winchester, Emotions, F/M, Fake Marriage, Fake/Pretend Relationship, Feelings, Fluff, Hair-pulling, Mutual Masturbation, Oral Sex, Rough Sex, Self-Doubt, Semi-Public Sex, Slow Build, Slow Burn, Smut, Vaginal Fingering, Wall Sex
Language: English
Status: Completed
Published: 2020-06-08
Updated: 2020-07-03
Packaged: 2021-03-03 21:46:54
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 21
Words: 62,458
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24602587
Author URL: https://archiveofourown.org/users/smolandgrumpy/pseuds/smolandgrumpy
Summary: She always thought her boss was an ill-tempered man, but when he presents her with a proposition she can’t quite deny, she gets to know him better. It’s not bad, right? Because all she has to do is being fake married to him for six months, sounds do-able, right? Right.
Relationships: Dean Winchester/OFC, Dean Winchester/Reader, Dean Winchester/You
Comments: 218
Kudos: 339





	1. CH01

_Shit, shit, shit._

She’s going to be late, so fucking late! 

Y/N hastily slips into her shoes, does a final check of her reflection in the mirror before she gets out of her apartment and hires a taxi. It’s not like she can afford it with the high rent in the city, but she can’t risk getting late into work because her boss would be beyond pissed and she’d like to avoid being at the receiving end of his wrath right at the start of her week. 

She’s still panting when she sits in the taxi. If she hadn’t been lost in thoughts and wanted to finish reading her damn novel while she drank her coffee, maybe then she wouldn’t have spilled it all over herself and wouldn’t have had to change into something else and she wouldn’t have been late. 

Mr. Winchester will be so pissed.

He’s known for firing people, exchanging them for someone who would be gone in under a week's time. She’s actually surprised that she made it this long. It’s almost a year now that she became one of his office assistants and while it’s a good job and a good paying one too, she thinks it’s fucking challenging. She needs that job and she can’t afford to get fired. Jack, her brother, is still in college and she needs to help him, since she and Jack — well, that’s all the family that’s still left. 

She quickly types out a text to Jack when she sees the taxi rounding up to her office building. 

_Y/N: Cross your fingers. I’m late. I hope I won’t get fired._

_J: Oh, no. I’m crossing my toes, too! You got it, sis!_

Alright. She takes a deep breath, gets out and pays the driver before she takes the elevator up to her floor. 

Arriving on the floor, she already hears someone yelling. The voice is deep, gravelly, it can only belong to one person that she knows of. He’s also the only one who’s allowed to yell around here, actually. 

Walking over to her desk, she sits down and starts up her computer. She hopes that by acting normal, nobody would know that she’s thirty minutes late, and she doesn’t even have a good explanation should someone ask. She couldn’t even lie about it because she’s an awful liar.

Mr. Winchester hates tardiness. She once watched him firing someone who was five minutes late. 

She doesn’t know what’s wrong with Mr. Winchester sometimes. Like, he’s all professional but every time she has to work with him, he acts all grumpy. After a year of repeatedly watching him being his grumpy self around her, she can’t help but think that he doesn’t really like her at all. But again, if he doesn’t like her, why didn’t he fire her already?

“Go away! You’re fired!” 

Oh god, it’s not even 9am and he’s already firing people. She sees Adam walk past her desk, his head low. Awe, that’s sad. She quite liked Adam. How long has he been here? About seven months? God, she wishes that she had the balls to stand up to that jerk Winchester.

Mr. Winchester walks out of his office and right into her view. She ducks her head, pretends to look occupied, which she actually is because she’s now logged in and skims through her emails. There are several of Mr. Winchester from this morning and she looks at the time stamps. 6.45am, 6.57am, 7.12am, 7.34am, 8.01am, 8.02am, 8.03am, 8.04am, 8.05am, 8.06am, 8.13am, 8.16am, 8.24am, 8.26am. 

_Shit._

She’s going to get fired for sure. _Say bye to your college degree, Jack._

His footsteps echo in the quiet office and it comes to a halt at her desk.

_Uh-oh._

Y/N doesn’t dare to look up.

“Where were you?” Mr. Winchester snarls. 

“I— uh,” She stammers, and then she looks up at him. His suit is neat, the scruff a little longer than usual, and he looks tired because his eyes aren’t as green as they usually are, which is a good thing because she always tends to get lost in them if she stares at them for too long, “I’m sorry, sir.” 

“I want to see you in my office,” He hisses, “And while you’re at it, get me a coffee, alright?” He turns around, walks back, but stops and tilts his head back again, “Please.” With that, he’s off into his office and slams the door shut. 

Hey, at least he said please, right?

Ruby looks up at her from her computer, “My god, what’s wrong with that guy? Can you believe that he’s one of the hottest bachelors of the year according to some magazines? The voters surely haven’t ever seen him like this.”

“Shush, Ruby,” Y/N says, “What if he has bat ears?” Really, she wouldn’t be surprised if he has.

Ruby does that locking motion with her hand on her lips. 

“But someone surely has got out of the wrong side of the bed.” She says, and adds, “I thought he spent the weekend in Vegas for that meeting? Didn’t it go well?”

“It did, apparently, but who knows,” Ruby shrugs, “Anyway, if I were you, I would go grab that coffee quick, Y/N. I don’t want him firing you.”

“Shit, right!” She gets up and storms into the break room to get the coffee and speeds back on her heels to Mr. Winchester’s office door, almost trips once but she managed to save herself gracefully.

She knocks and enters, and to her surprise, someone else is in the room as well. 

Sam Winchester, the company’s lawyer and brother to Dean Winchester. 

Sam stands by the window, looking out into the streets while her boss is hunched over his desk, his forehead on his arms. 

Something’s wrong and she’s afraid to ask what it is. So instead of asking, she steps in, “Your coffee, sir.”

“Huh,” Mr. Winchester looks up from his desk, “Yeah, thanks. Please take a seat, Y/N.”

Hesitantly, she walks closer, clears her throat as she sets the coffee on his desk, and sits down, “Mr. Winchester, please, whatever it is, I promise that I won’t make the same mistake again. My being late today was really an accident, I spilled coffee over myself and had to change my clothes, it’ll never happen again, please. I need this job.”

“Jesus, Y/N, relax!” Mr. Winchester groans, and Sam Winchester looks at his brother with amusement in his eyes, “My head’s hurting. Shut up, please? You won’t get fired, I promise.”

“Oh,” 

“In fact, I have a proposition for you.” Mr. Winchester stands up and walks around to her side of the desk, leaning against it, “I want you to be my fake wife.”

She frowns, thinks that she hasn’t heard him right, “What?”

“Look, I’m not really happy about it either,” He starts to say, and she frowns some more for fucking good measure.

“Wow, thanks,” Y/N huffs out, “What a great compliment.”

“No! Christ!” Mr. Winchester rubs over his scruff with his fingers. The scratching sound is loud in the otherwise quiet room, “I didn’t mean it like that.” 

“Why do you want me to do that?”

“Yeah, why, Dean?” Sam cuts in and he starts to chuckle, which prompts Dean to send his brother a glare. 

“Shut up, Sammy.”

He turns back to her, “Look, the meeting in Vegas went well, alright? I got Chuck Shurley to let me buy shares of his company. The thing is, after the dinner, we went for a drink, and next thing I know, I was married to his fucking sister.”

Y/N really tries not to laugh, “Wow.”

“Yeah,” Mr. Winchester scoffs.

“So, did you get ordained by Elvis or something?” 

“Y/N! Jesus! Focus!” He yells, which made her flinch, “I’m married and now she wants at least a quarter of what I own if I want to annul the marriage. She fucking set me up, but I can’t really prove it.”

“Amara Shurley is a very beautiful and rich woman,” She shrugs, because it’s true. Every guy wants to be with her, she wonders why Mr. Winchester doesn’t. 

“Your point being?” He raises an eyebrow at her, “Just because she’s beautiful doesn’t mean that I have to want to be with her, does it?”

“No, sir. But I’m wondering why you want me to pretend to marry you when you are already married?”

“We can show Amara another marriage certificate, one that says that we married a month ago, right Sammy?” Mr. Winchester asks his brother, but his eyes are on her. 

“That’s right. It’s already signed by all parties. All you have to do is sign it. I’m waiting for the court dates as we speak,” Sam Winchester says and shows her the apparent very important piece of paper.

There are signatures of Mr. Winchester. His brother and Ruby as witnesses. Ruby? Fucking Ruby? Oh my god, and she didn’t even warn her!

“Ruby’s your friend besides work too, isn’t she?” Mr. Winchester asks. 

“Yeah,” Y/N nods.

“Good,” Mr. Winchester says, and adds, “What do you say? Would you do me the honor of becoming my fake wife?”

Her mouth stands slightly agape, she blinks, “This is stupid. Why would you do that? It’s not even legal, is it? Why me?”

“I’m pretty desperate, as you can tell,” Mr. Winchester answers short. And it hurts. It hurts damn bad. Not that she expects anything less. And then he goes on, “Look, I know that it’s a big breach into your privacy but I can guarantee you that you’ll get rewarded for it. I’ll pay you double and you don’t even have to work while you’re married to me.”

But she likes to work! Well, yeah, sometimes he can be a dick but she actually really likes to work. She doesn’t say it, though. Instead, she asks, “How long do we need to be married for?” 

“Six months.” Sam Winchester cuts in.

“Six-what?!”

“Yeah, that’s the only way it won’t look suspicious.” 

“Ah, great. Because we don’t want that, do we? We don’t even live together! I don’t know you! This is going too far.” She’s mad. Can’t lie about it.

“Y/N, please. You’re the only one that I know who doesn’t get irritated by my mood. You know how I like my coffee, you know where I like to eat out, you know my schedule, you’re the only one who really knows me here!”

Sam Winchester clears his throat.

“Calm down, Sammy, alright!” Mr. Winchester rolls his eyes. 

She bites her bottom lip, thinks hard about it. It’s not like she can not _not_ agree to it. It’s double pay for six months! Jack could finish his degree. But she asks anyway, “What are the conditions?”

“I have the contract ready, too,” Sam Winchester says, and hands it to her, while she begins to read it, he goes on, “You’re going to live with Dean as of today,” The younger Winchester says matter of factly.

“Today?” She stands up so abruptly, the chair screeches along the floor, which makes everyone in the room flinch, and Mr. Winchester’s hand goes to his temple. “Sorry,” She whispers.

“Yeah, today. You’ve been married for one month, think it’s time you move in together, no?” Sam grins.

“Okay, and what else?” Y/N crosses her arms over her chest. 

“Monogamy.” The taller Winchester smirks, “No sex or flirting with anyone else for the next six months.”

“What?” Mr. Winchester scoffs, “You didn’t tell me that, Sammy!”

Sam Winchester just shrugs, “I mean, it actually goes without saying. You’re married, that’s what married couples do when they’re in love, being faithful. At least in the first six months I’d hope so.”

Mr. Winchester rubs over his scruff again. He does that a lot when he’s thinking. After a short while he looks at her, “Okay, I can do that, can you?”

How can she say that it's a piece of cake for her because she doesn’t have a healthy social life anyway? All she’s been doing is working and sleeping for a year now. But of course she doesn’t say it. Instead, she says, “I can,” and looks at her boss smugly and he cocks her an eyebrow.

“So that we’re clear, you’re going to act like a lovey dovey couple for the next six month.” Her boss’s brother states.

“Yes,” Mr. Winchester and her say it in unison.

“Great,” Sam Winchester hands her a pen, “If you could just sign here and here, Y/N.” He points to the places on the certificate and contract.

She signs the documents and the taller Winchester puts it away into his case. “Right, I’ll see you guys around,” he calls out before leaving.

“So, Mr. Winchester—”

“—Please call me Dean. We’re married now.” He lets out a tired chuckle.

“Right,” She sighs.

“Look, I’m sorry about it, alright? I’m not out to make your life miserable but maybe if we work on it together it’ll be half as bad as it seems right now?”

“Maybe, yeah.” She agrees. “So, what do you want me to do?”

“You go home and pack your things. I’ll send Gabe to pick you up and bring you to my penthouse.”

Penthouse. How fancy. 

“And don’t worry, the rent for your apartment will be covered.”

“Okay,” 

She walks out of the office with a weird feeling in her guts. When she arrives at her desk Ruby’s grinning.

“You fucking knew!” Y/N hisses at her friend.

“Oh, come on,” The other girl huffs out, “What’s so bad about being married to the hottest bachelor in the business world?”

Well, Ruby’s actually not entirely wrong, but he’s her boss. It will _always_ be awkward. 

“Ask me again in six months, will you?” She says, shuts off her computer and is about to leave when Ruby eyes her, “What?”

“Where are you going?”

“I have to go pack my things.”

“Why?”

She sighs, “Well, I have to go live with him now.”

“You what?!” Ruby damn near squealed.

“Shhh!” She hushes her friend and looks around, smiles when she sees Donatello looking over here with one raised eyebrow, “You know that you can’t talk about it, right? You probably signed a contract.” She doesn’t really know it but given how Sam Winchester is good at what he’s doing, she guesses that they cover Dean’s ass thoroughly. Not that she wouldn’t mind covering that ass herself...

_Focus, Y/N!_

“Yeah, I signed something. I didn’t read it because damn, that young Winchester is yummy. I’d like to climb him like a fucking tree.” 

_Great._

“My god Ruby, you should always read what you sign!” 

“In my defense, I was lost in his dimples, okay? Anyway, it’s good if you live with him, no? You can see if he really has a stick up his ass when you walk in on him showering or something like that.”

“Oh my god, I need to leave.” She grabs her bag and walks to the elevator when Ruby makes kissy faces at her. She sticks out her tongue and in that moment, Dean walks out of his office and frowns at her. 

Monday has just started fucking great, hasn’t it?


	2. CH02

There’s a knock at the door in the afternoon and she opens up to Gabriel, Dean’s personal driver and handyman. She has known him for a while now, having started at the company almost at the exact same time. Gabe’s secretive — probably why Dean hired him in the first place — and he’s really easy to talk to. 

“Boss said I should move your things to his apartment.” Gabe says and steps in. 

“What else has he told you?” She closes the door and follows Gabe over to where her suitcases are. 

“Nothing much. You’re married or something. But I signed a NDA, so, no worries,” He shrugs like it’s no fucking deal, which makes her wonder what else he knows. She wonders what else Gabe witnessed while driving around for Dean.

“Is that all?” He asks and points his finger at her two packed suitcases.

“Yeah, I travel light.” She smiles, feels a little embarrassed actually. But that’s how it is. Everything she owns fits into two lousy suitcases. It’s actually quite sad when she thinks about it. 

“Damn, you could have taken the subway with them suitcases. There’s no need for me,” Gabe says it with an amused tone to his voice. 

  
  
  


*

  
  
  


Gabe drives into the parking garage of the building Dean lives in. He tells her to call the elevator and take the one far left because that one will go to the top floor without making unnecessary stops. He then takes out her luggage and follows her. 

As they are standing in the elevator, the stupid music starts to play and she hates that. Hates lame elevator music, because it makes everything so much more awkward. Dean even has his own elevator. It’s a little ridiculous when you think about it. 

They arrive and Gabe shows her the way, which is probably not really hard because there’s only one door that looks like an apartment door. All the other doors had signs on them that say  _ Keep out! _ or  _ Private! _

Gabe rings the bell and she waits behind him. She can’t lie, she’s a little scared. Like, he’s her boss and he’s so damn grumpy all the time and she’s afraid that he’s going to fire her even in his own home. 

Dean opens the door, his hair’s ruffled, his jacket and tie are off, the top two buttons of his shirt are loose, and his sleeves are rolled up. The shirt has those crinkles on them as if he just took a nap. Maybe he did? He was complaining about a headache earlier. 

“Hey,” He says and opens the door wider, for Gabe and her to step through, “Thanks Gabe, that’ll be all.”

“Right,” Gabe nods, “I’ll be in the car ready to leave when you are.”

Dean gives Gabe a courtesy nod before he closes the door behind him. He then turns to her. It's really awkward. She wonders if she’s made a mistake in agreeing to be his fake wife. 

He has both his hands in his pockets when he looks at her and asks, “You okay?”

“Yeah,” She manages to give him a weak smile. She can’t tell him that she’s in fact, not really okay of course, that she’s in fact, nervous as hell. 

“Come on, follow me,” Dean starts to walk through the penthouse and she needs to speed up to be able to keep up with him. His legs are incredibly long and hers are not, “I’ll show you around.” 

They walk into a big open space. There’s a black sofa in one corner. It faces a ridiculously big screen tv. There are also two big comforter chairs which she frowns a little at. It’s not that they don’t look nice, they just don’t really fit into the setting. 

Dean senses her confusion, “I bought them for when Sam’s over. Watch,” He grins and walks over, sits in one and reclined himself. When he settles, he pushes a button and there's a buzzing sound, “It massages your back,” He says, a smile on his face that’s brighter than the sun. She couldn’t not laugh at that. 

“Right,” Dean says then, “Gotta get out before I let myself be sucked into it. It’s hard to get out once you relax too much.” 

She can imagine and actually, she can’t wait to get in there herself.

He continues to walk ahead and they get into a kitchen area. The fridge is more than twice as big as the one she has at home and it’s stocked up, too. Either he went to the store before or he has someone to do it for him. She thinks it must be the latter. She just can’t imagine him walking through the aisle wheeling a cart in front of him.

After the kitchen, he walks along a hallway and points to the rooms. 

“That’s my study, I don’t use it that much but there’s a computer and printer. If you need something, you can use it.”

The door next to the office is the guest bathroom. It’s bigger than the living room of her apartment. 

They walk further along the hallway and come to stop at two doors on either side of the narrow hallway.

Dean opens up the door to her right, “That’s your bedroom,” They walk in and it’s spacious as hell. She thinks it’s even bigger than her whole apartment. Everything is kept in a warm mix of white and beige, “And that’s your bathroom.” He walks through to the en-suite and she can see that the tub is huge. 

He looks at her, sees her mouth standing agape and has to grin.

“What?” She asks, feeling a little flushed knowing that he’s been watching her. 

Pressing his lips into a tight line, he grins a little. There are teeny tiny dimples showing, “There’s a gym on the first floor of the building, you’re free to use it if you want.”

“Okay,” She follows him out again and wonders what is behind the door that he hasn’t mentioned, “And what’s there?”

“That’s my bedroom.” He says simply, and he’s already rushing back into the living area, and fuck why are his legs so damn long. She is glad that they’re bowed, he would probably be even faster if they were straight.

“Dean, slow down, I’m not that fast,” She has to call out because he’s already at the door to the balcony. 

He laughs, “Sorry, I’m just so used to walking around with Sam and he never has a problem keeping up with me. I’ll try to go slower, okay?” He waits until she reaches him.

“That'd be great, thanks.”

“Come on, you need to see this,” There’s a boyish smile decorating his face. It’s nothing like the grumpy Dean she knows as her boss. He’s genuinely content, and it shows. 

He opens up the door to the balcony and holy shit, it’s not a balcony. It’s a freaking terrace. There’s a hot tub on the far left side, overlooking the city.

“Nice, isn’t it?” 

“Yeah,” She agrees, “It really is. How often do you get to enjoy it, though?” It’s a legit question because she knows how much he works. 

“Maybe I’ll get to enjoy it more now that you’re here.” His voice is a little soft when he says it. Before she can even ask what he means by that, he clears his throat, “Right, I really need to go back to the office now. Will you be okay? I’ll try not to stay too late, alright?” 

“Sure,”

“Make yourself at home. It’s yours now, too.” He’s about to turn around but then he stops, “Really missed you in the office this morning. Ruby doesn’t know how I drink my coffee.”

“It’s not hard? You drink it black.”

“Yeah, but hers is different.”

She doesn’t really know if he’s shitting her. Dean’s so hard to read sometimes. 

“Dean, the coffee is the same!”

“Fine,” He rolls his eyes, “But anyway, just so you know. You’re missed in the office. Not just because of the coffee.”

“Now you’re just kissing my ass.”

Dean snorts out a laugh before he turns around and picks up his tie and jacket. He walks to the door, turns around again, “Call me when you need anything!”

She can’t even say  _ okay _ because she can already see that the door closed. 

  
  
  
  


*

  
  
  
  


Two suitcases are easy to unpack. Half of her new closet is still empty. She didn’t even need more than an hour. 

Walking out into the living room, she sees the comforter and decides to spoil her body with a massage. 

She sits in, reclines herself and pushes the same button Dean did before, and immediately a buzzing sound fills her ears as her back starts to vibrate. She lets out a squeal at first but soon starts to relax and it does feel really good. She closes her eyes and almost drifts off when she feels another kind of vibration in the back pocket of her pants. 

Taking out her phone she looks at her screen.

Dean.

_ D: What are you up to? Find everything alright? _

Y/N frowns. Because she sees the time and knows for a fact that he’s in a meeting right now because she organized that meeting.

_ Y/N: Aren’t you in a meeting? _

_ D: Yeah, but I’m bored. _

She doesn’t even know that he’s a texter. Every time she saw him with his phone in his hand, he talked to someone. He never just has his phone in his hand and fucking texts.

_ Y/N: If you’re really interested, I’m sitting in the comforter and I’m enjoying a massage. _

_ D: Jealous. _

_ Y/N: Was thinking about taking a bath in the hot tub. I’m allowed to use it, right? _

_ D: You are. But I would wait til the evening. The view is nicer then. _

_ Y/N: Okay. _

But he’ll be here in the evening and he’ll see her in the tub. Ugh. 

_ D: Right, just wanted to see if you’re okay. Since you are, I’m gonna go back to listening to whatever Donatello has to tell me. See you later, Y/N. _

_ Y/N: TTYL _

_ D: TTYL? _

_ Y/N: Talk to you later _

_ D: Oh, TTYL _

She snorts out a laugh, thinks that texting-Dean is kind of adorable.

  
  
  


*

  
  
  


After a relaxing massage, she decides to take a shower. Mainly because she still hasn’t showered after she poured coffee all over herself this morning. 

The shower’s huge too, the water pressure is excellent. The nozzles (and boy are there many of them), hit her sore spots just right.

She dresses herself back in some jeans and shirt. Normally if she’s at  _ her _ home, she’d walk around in only a shirt but she’s practically a guest around here — even if Dean insists that it’s her home, she doesn’t trust it yet — and she doesn’t really know how her boss would react seeing her walking around in his apartment in only her underwear and a shirt. 

Taking her book that she didn’t get to finish this morning out into the living room, she grabs a cup of coffee before she makes herself comfortable and cozies herself up on the couch to finish her book. 

Just when she reaches the second to last page, Dean walks in, his tie already loose around his neck, “Honey, I’m home!” He smiles when he sees her staring at him, “I always wanted to say that once in my life.”

“You’re early,” She says, pushes at the button of her phone to realize that it’s almost 6pm. Normally he’s still at the office. 

Dean switches on the light for her and she doesn't even realize that it starts to get dark out. 

“Yeah, I still have a headache. It’s been like that since I woke up after the night I married Amara. Didn’t feel like working longer and leave you alone either.” He comes to sit next to her and she catches the smell of his cologne mixed with his musk. He smells delicious even after a long day and that’s not really fair. 

“Should I go get some painkillers? You just have to tell me where they are kept.”

“Nah,” He sighs, “I’ll just take them before I go to sleep. What are you up to?” He asks her, and she sees that he’s eyeing up her book that she’s still clutching in her hands. 

Her face starts to flare up. 

“Just reading a book.” She says it in an easy way, tries to sound nonchalant about it but she knows that she fails.

Dean catches the cover before she could hide it and he starts to grin, “You sap.” He stands up again when he sees that she starts to feel uncomfortable if they didn’t change the subject soon.

“What do you want to eat? Does Pizza sound alright? I’m not in the mood to cook tonight.”

That’s when it dawns on her that she’s playing his fake wife and maybe she should have cooked him something for dinner? Because that’s what wives do right? She doesn’t fucking know because she hasn’t even been in a relationship long enough to cook anything for anyone. Except that she sometimes used to cook for Jack.  _ Oh my god _ , Jack! She still has to tell him what happened! 

She gets up from the couch, abandons her book and walks to Dean who’s already in the kitchen leafing through take-out leaflets, “I’m sorry, I should have cooked you something,”

He stops in his tracks to look at her, one eyebrow raised, “What?”

“Yeah, I’m supposed to be your fake wife and I’m supposed to cook you something.”

Dean sighs, “Y/N, really. That’s not why I fake married you. You don’t have to do anything in fact. It’s okay alright? I’m a big guy and if I want something cooked, I can do it myself.”

“Okay,” She says, still feels a little guilty about it, though. And Dean seems to sense it because he drops the leaflets and walks over to her, places his hand on the back of her neck and she catches the whiff of his cologne. It makes all the hair on her body stand up and she gets light headed. 

He lowers himself a little, looks her in the eye, “You don’t have to do anything you don’t want to, you understand? Hey, look at me.”

She does, looks straight into his green eyes. Dean Winchester has freckles. She never noticed them before, was always distracted by the green of his eyes. 

There’s a moment of silence, and she doesn’t know if he feels it too. Feels a magnetic force that pulls her towards him.

“Are we good?” He leans in closer and she can feel his hot breath.

“Yeah,” She nods.

“Good,” He says, but doesn’t quite move away yet, if anything he moves even closer. He’s closer to her than he’s ever been, “Because I want you to feel comfortable around me, okay? I’m really not your boss when we’re together. I want you to be yourself, can you do that?”

“Sure,” 

Dean smiles, showing his white fangs. Her heart races a little more. She would love to feel the teeth on her skin.

_ Y/N, what’s wrong with you? _

He lingers a little longer, his hand still firm on the back of her neck and she feels like he’s staring into her soul. He licks his lips before he speaks, “Are you hungry?”

“Not really,” 

She’s really not, at least not yet. She’s too confused to eat. Confused about the fact that she feels that she’s attracted to her own fucking boss. Someone who she’s faked married to!

“Right, how about you take that bath in the hot tube that you talked about? I’ll go take a shower and we’ll order later, huh?”

She looks out of the window and grins, because the sun’s going down and the view’s really is fabulous, “Sounds good to me.”

  
  


*

  
  


She slips into her room to change into a bathing suit. She doesn’t really have anything fancy, only a simple black bikini but she’s not really here to impress him, is she? She’s not really here to do more than being his fake wife, right? Right.

When she walks out to the terrace, Dean must already be in his room because she can’t see him but she did find the tub heating up and bubbling away. There’s a bottle of wine and glasses on the table next to the tub. She smiles when she thinks that he prepared it for her. She wouldn’t have guessed that he would do things like this. At least not boss Dean that she knows.

She steps into the tub and lets herself sink lower. Closing her eyes, she embraces the feel of floating outdoors.

“You didn’t pour yourself wine?” Dean’s voice suddenly jerks her back to reality. 

Y/N opens her eyes to see Dean standing there, wearing a simple shirt and sweatpants. His hair’s still damp from the shower. She’s astounded, he looks completely different. Still good, but different. More casual, more relaxed. 

“I was too excited to get in,” She smiles at him.

Dean mirrors her smile before he pours the wine for her, “You must have wine in there in order to get the full experience.” He walks over to hand it to her. 

“Thanks,” She says, and thinks whether she should ask if he wants to join her? What’s the proper hot tub etiquette? “You want to come in?”

He chuckles, “Nah, maybe some other time, I’m enjoying the view from here.” He pours himself some wine and sits down, stretching himself before his face settles into a smirk. 

She thinks it’s weird that he said he wants to enjoy the view but he’s sitting facing her. 


	3. CH03

They enjoy their glass of wine in silence before her stomach starts to growl. It growls the loudest she’s ever heard. Maybe it’s because she hasn't had anything to eat since this morning, and her stomach rebels against the wine as it’s the only thing in there. She should have known better.

Dean must have heard it because he starts to chuckle, “What toppings do you like? I thought we could share one.” 

“Sure, but don’t judge, please?” She says as she stands up, sees Dean’s eyes on her and feels the urge to cover up. He gets up from his chair and takes the towel she brought out with her, holds it up for her to cover herself.

When he looks at her again, he has one eyebrow cocked, “Why should I judge?”

“Uh, because I quite like pineapples on pizza,” 

“I don’t judge,” Dean scoffs, and adds, “But I really think  _ that  _ should be illegal,” He laughs, but he doesn’t say anything more, and goes in to order their pizza. 

Y/N slips in while he’s on the phone and goes straight to her room, and changes into something comfortable. Now that she’s seen that he wears sweats, she’s happy to match him. It’s actually pretty weird seeing Dean like this because the only clothes she ever saw him in are suits, it makes her think that he even sleeps in them. She wonders if he has other clothes at all.

When the pizza arrives, Dean moves the glasses and bottle into the living room and asks her what movie she wants to watch, but she really doesn’t mind so she lets him choose. Dean zaps through Netflix and settles on Bird Box. 

While the movie starts, he hands her some napkins, and she’s wondering if that’s enough, because she’d hate to ruin the nice couch. He must have sensed her hesitation because he’s smirking, “It’s okay, you don’t wanna know what I managed to spill on this couch already,”

“Ewww,” She mocks, cringes her nose and he snorts out a laugh.

_ It’s easy _ , she thinks. It’s easy to let herself go. It’s easy to be here with him and just talk about anything outside of work. She comes to the conclusion that Dean’s not such an asshole after all. In fact, he’s a real gentleman. And that’s not really good, is it? It makes her feel things she shouldn’t feel.

She shakes the thought out of her head and takes a slice of pizza out of the box. It’s then that she realizes that the whole pizza is riddled with pineapples. She frowns, “I thought you didn’t like pineapples on pizza?”

“I don’t,” Dean shrugs, takes a bite and pretends to wrinkle his nose before he grins with his mouth full and continues to eat. 

Y/N doesn’t think she makes it far into the movie because her eyelids are getting heavy halfway through. It’s the most illogical, most boring thing she’s ever seen, but she didn’t want to hurt his feelings so she tries to watch it. 

Last thing she remembers, though, is that she’s half leaning against Dean before she fell asleep. 

  
  
  


***

  
  


Y/N wakes up in a bed. It’s clearly not hers. It took her an embarrassingly long time to realize that she’s in Dean’s apartment and that she’s in  _ her  _ bedroom. 

Oh no, she remembers eating pizza with Dean, remembers falling asleep to the stupid movie. He must have carried her to her bed. 

Her own fucking boss had to carry her to bed! If that’s not embarrassing she doesn’t know what is. 

She scans the room and her eyes settle on the clock on her nightstand. It’s already past 8am. She slept like a baby through her alarm but in her defense, the bed is so fucking comfortable, more comfortable than her own, and it’s only a fucking guest room. She wonders how comfortable Dean’s bed must be. How he can even wake up and get out of it every morning astounds her.

And then, the thought of being late for work crosses her mind before she realizes that she doesn’t have to go in. Realizes that she didn’t sleep through her alarm because she didn’t set one in the first place.

Grabbing her phone, she sees that there’s a text from Ruby.

_ R: How was your first night? Did you consummate your fake marriage? *wink wink*  _

Then a text ten minutes later.

_ R: Oh my god, it should have been a joke but you did, didn’t you? He’s in a remarkably good mood. Didn’t bitch about the coffee I brought him at all! _

Ah, Dean’s already at work then. He’s usually there before she turns up, and now she knows why. It’s only about a ten minutes walk from his apartment. 

_ Y/N: Relax, nothing happened. _

_ R: Ah, there she is. _

_ Y/N: I slept in. The bed is so comfortable! _

_ R: His bed I’d hope! _

She snorts out a laugh. 

_ Y/N: No, I have my own room that’s bigger than my apartment. _

_ R: Ugh, maybe I can come see you? Wanna see how the most not eligible bachelor lives. Or send me pics! Oh shit, he called out for me. I need to go. But I swear, whatever you’ve done to him. Do it again! I like to work for him when he’s not constantly yelling at people. _

She chuckles at that. She doesn’t answer Ruby though, instead she sends a text to Jack, telling him that she’s got another job that would secure him his degree and that everything’s okay.

Climbing out of bed, she decides to get coffee. It’s weird not having to go to work and she kind of misses it a little. 

Y/N walks out into the kitchen where there’s still a faint smell of his cologne and coffee in the air. A deadly combination for her brain apparently, because it makes her insides tingle in all the right places. She looks around and immediately spots a yellow sticky note left on the machine. 

It’s Dean’s handwriting. She knows it from all the scribblings he leaves on her desk when he already shut off his laptop and thinks about something that she must do for him the next day. 

_ The machine is easy to handle. On, off. That’s it.  _

_ I’m sorry I made you watch that movie. If you want to know, it didn’t get better after you fell asleep. Two hours of our lives, wasted. I’ll see you tonight, maybe we can watch something else — D _

She’s smirking. He really took his time this morning to write her a fucking novel. It really baffles her that he goes out of his way for her and it really seems like he genuinely cares to make her stay with him as comfortable as he can. Well, it does benefit him too, come to think of it.

  
  
  


*

  
  


After another round on the massage comforter, she walks into her room to find a message from Jack. 

_ J: I hope you don’t sell yourself for my benefit. But I trust you. Miss you x _

She has to smirk and immediately types an answer back.

_ Y/N: Just stay in college and make me proud, alright? _

Just when she’s about to put her phone away, it lights up with a call.

Dean.

“Hello?” She says, wondering if she should add  _ sir  _ to it at first but decides to drop it.

“Hey, you slept alright?”

She smiles, “Yeah, thanks. It’s the most comfortable bed.” She bites on her tongue so as to not ask him about him carrying her back to said bed.

There’s a light chuckle on the other end, “Good. Listen, I went over my schedule today because Ruby didn’t do it for me, and saw that I can’t have a movie night this evening like I wrote on the note,” He pauses to think, “You found the note, right?”

“Yeah, I did.”

“So, you maybe did know this because you arranged the invitation and you put it into my calendar, but I didn’t until about twenty minutes ago,”

She thinks hard about his schedule, remembers that there was something. An event. Some kind of gala. 

“But instead of watching a movie, what would you say to me taking you out?” He says, “I called them and managed to do a last minute adjustment to my invitation.”

“Oh,” She huffs out, knowing where Dean wants to go with that.

“Thought it’d be a good opportunity to show them my wife. Are you in?”

He still asks, even if he actually doesn’t have to? Because yeah, she obviously can’t be a fake wife in private. The world needs to see it. Amara needs to see it.

“I guess,” She mutters. She is actually not really sure if she can pull that off. Her heart beats faster just  _ thinking _ about walking on a red carpet.

“Y/N, you don’t have to, you know,” It’s as if he senses her dread, “I don’t want to do anything that makes you feel uncomfortable, but we should at least try to look like a happily married couple and we can’t pretend if you don’t want to.”

“No— I mean, it’s okay, I’ll do it,” Her voice is more firm this time. She wants to. Wants to show him that she can do it. 

It shouldn’t be hard, right? She’s been with a man before. She knows all that hand holding stuff. And Dean’s paying her double for god’s sake. What’s an evening of being flirty with him? It’s not like he is an old greasy man. Well, maybe that would be better? Maybe then she will not risk falling for him? Because that’s what is going to happen if she’s not careful, she just knows it. And then she’ll get her heart broken. Even though a broken heart is a little price to pay if it means that Jack can finally start his own future, come to think of it.

“Okay,” There’s a huff of breath, he’s smiling, she can hear it, “Good. I’ll get Gabe to drop off my card, you can go shopping for a dress. The card has no limit, just buy whatever you want, alright?”

She grins smugly, “I need shoes, too.”

“Buy all the things you want.”

“Alright, sir.”

“Y/N, stop calling me that. Unless,” He pauses and there’s a playfulness in his voice, “That’s what you like.”

She’s glad it’s not a video call, so he isn’t able to see that her face is burning up. She doesn’t say anything and Dean takes the hint.

“Right, I have another meeting, I’ll see you around 7pm. The gala starts at 8pm.”

“K, bye Dean.”

“Have fun.”

  
  
  
  


*

  
  
  


Y/N’s standing in her room as she waits for Dean to come back. He’ll probably need to shower and get dressed too. 

Gabe came by to drop off Dean’s Centurion card and he walked straight into Dean’s bedroom to drop off Dean’s tux onto his bed. She never had such a card in her hands, it feels heavy, made of platinum, not like her cheap plastic one that she only uses once in a blue moon.

At first she didn’t know where to go because she hadn't been dress shopping for a gala before. She wondered if H&M would be a good choice but then thinks that it probably wouldn’t. While she was out shopping she looked into shop windows and came across a beautiful long sleeved sequin pattern dress in gold. 

She never knew gold would look good on her but the shop assistant was so nice, even though she knows it’s that woman’s job, she felt really good in the dress and it wasn’t over the top with the price so Dean should be okay with it. She couldn’t resist buying matching shoes, too. 

Later, she splashed out some money for lingerie that she could wear under it and hoped that Dean wouldn’t mind. He told her to buy whatever she likes, so.

And now, she’s nervously pacing around her room. Her pacing only stops when she hears footsteps approaching.

There’s a knock at her door, “Y/N, you okay?”

“Yeah,” She manages to say.

“Good, sorry I’m a little late, had to pick up something on the way. I’ll shower and get dressed. Meet you in the living room in thirty minutes?”

“Sure,”

She hears him opening the door to his room.

Thirty minutes. Ugh. She hasn’t even applied makeup yet. She’s so nervous.

After a last check in the mirror, she walks out into the living area, her heels clicking on the marble flooring. She’s not used to wearing such high heels, and prays that she won’t stumble and fall flat on her face. 

As she rounds the corner into the living area, she sees Dean already waiting for her, dressed in a fitting tux and smelling so fucking delicious. He looks like he’s just stepped out of a glossy magazine spread and that’s not fair. She can already see the press giving them a caption for their picture together. It reads,  _ DEAN WINCHESTER COULD DO SO MUCH BETTER.  _

Y/N can feel Dean’s eyes on her. They’re wide and his lips part slightly before they curve up into a smile. It’s bright and white. She’s smiling too, can’t  _ not _ smile when he’s looking at her like that. Looking at her like she’s the only one that matters. She’s not used to it at all.

“Wow,” Dean breathes out, “You look beautiful.”

She was already blushing before but now her cheeks heat up a little more, “Thank you. You’re not bad yourself.”

Dean has to chuckle and then all of a sudden, he runs back to his room, “I’ll be right back,”

After about a minute Dean reappears clutching things in his hand. One of them is a pocket square. He went in and picked out a color that matches her dress. She has to grin at that.

He places it inside his jacket but he seems to struggle, “Can you help me, I—”

“Of course,” She grins, and steps closer to him, arranging the pocket square so that I’d look nice. Patting his pocket, she leaves her hand on his chest when she’s done, feels his heartbeat underneath her palm. She can swear it beats a little faster than usual, not that she knows his resting heart rate. “All set.” She says and Dean grins at her. 

“Okay, now my turn,” Dean licks his lips and clears his throat, and she can’t help but wonder what he means by  _ his turn _ .

She doesn’t have to wait long, because Dean opens up the little box he was still clutching and she can see the princess cut diamond engagement ring with a matching wedding band. 

“Dean, no.”

“Why, Dean, yes.” He chuckles, takes them out, and takes her left hand in his. “Y/N, will you give me the honor of being my fake wife for real now?” 

Y/N has to giggle at that, “Yeah, of course,”

He smiles, slips the ring onto her ring finger and to her surprise, they fit perfectly. She looks at Dean, raises her eyebrow, “Let me guess, Ruby?”

“Yeah,” Dean smirks, and then he shows her his left hand, “I have one, too. So, you ready?”

“Not really?” 

“That’s the spirit,” Dean places his hand around her waist, pulls her close and kisses her cheek softly. 

It does nothing to calm her down because she’s even more nervous now. 

“You gotta try to keep me from falling, okay?,” She says as he moves his hand to the small of her back, and guides her to the door. 

“I would never let you fall,” Dean shows her a small smile and they step into the elevator. 

In there, she eyes him up again, can’t quite take her eyes off him. He looks so good with the slight scruff and the freckles, the crinkles around his eyes deepen the longer she stares at him. 

“What?” He asks her, raises an eyebrow.

“You look good, Mr. Winchester,” She says with a smile.

“You too, Mrs. Winchester. Most beautiful girl I’ve ever seen. And I’m not lying.” He leans in, places another kiss on her heated cheeks before the elevator comes to a halt. 

He helps her get out and Gabriel’s already waiting, holding the limousine door open for them.


	4. CH04

When they arrived at the venue, they had to wait in the limousine line for the people to move along, one after the other. It takes longer because of the photographers and interviews the guests are holding on the red carpet. 

Dean senses her anxiety and grabs at her hand. He threads his fingers through hers, his thumb massaging at the back of her hand, “You okay?”

“Yeah,” She says, even though her mouth feels dry and her heart is near exploding. She’s really not made for the spotlight. 

It’s moving quicker than she thought it would and then suddenly, she feels him squeezing her hand, “Ready?”

She takes a deep breath and nods. Dean nods back with a small smile. Maybe it’s just her imagination but she thinks that he’s nervous himself.

Someone pulls the door open and Dean gets out first, she looks out from the car, sees how he stands there, buttoning up his suit jacket, nodding at the photographers with a big smile decorating his face. He’s used to it, she can tell. When he finishes buttoning up, he holds out a hand for her, and she knows that it’s her cue to get out as well. 

Immediately, she’s blinded by the flashlights. Oh god, it’s worse than she thought it would be. She tries to smile as Dean weaves his arms around her waist, guides her towards where more photographers and interviewers are waiting. 

“You’re doing great,” He whispers through his smile.

“I hope you know where we’re going because I can’t see,” She whispers back and Dean has to laugh at that. 

He walks her to a marked spot and they stand there, intertwined. Reporters are shouting Dean’s name and she really doesn’t know how he can still keep his cool. She’d like to yell at them for being so loud and shouting out all at the same time. It makes her head spin.

“Who’s that beautiful woman by your side, Mr. Winchester?” Someone yells out from the back.

“That’s my beautiful wife.” Dean’s voice is equally loud and he looks down at her, smiling a warm smile, his hand around her waist as he pulls her a little closer to his body. 

At the mention of the word  _ wife  _ everyone seems to gasp and the flashes stopped for a second.

“How long have you been married and how come you never brought her to events before?” A female reporter asks.

“Yesterday marked one month, and my wife is a private person, she doesn’t like being the center of attention.” 

She nods at that.

“How did you two meet?” One reporter shouts.

Dean chuckles with a boyish smirk, “She literally bumped into me in the streets and I was a goner since.”

“Tell us more!” The reporter asks.

“I don’t think we have that kind of time,” Dean jokes, and grins smugly.

“Mrs. Winchester, would you consider yourself lucky to be married to the sexiest business tycoon?”

Y/N seizes her opportunity, chuckles a little, “I would consider him to be lucky that he’s married to me,” She says and places her hand on Dean’s chest, looking up to him lovingly. Dean smiles down at her, the crinkles around his eyes deep. She makes sure that the hand on his chest is her left one, they can all see the rings.

“I love your dress!” One photographer shouts out.

“Thank you,” She replies, feeling a little proud.

Dean nods his agreement, “A dream in gold, isn’t she?”

“Can you two share a kiss for us?” A photographer yells out and several of his kind agree loudly.

Dean looks down, he smiles but he raises an eyebrow at her, as if to ask if it’s okay. She winks at him and his eyes go wide as his smile gets warmer before he lowers his face to hers. 

She’s prepared for a kiss but not for her heart to jump as soon as his lips touches hers. 

Y/N instantly turns to putty in his embrace and when Dean breaks the kiss and looks her in the eyes, she sees them glistening. Just when she thinks their moment is over, he dives in again, kisses her a little bit harder, his tongue teasing at her bottom lip and she grins into the kiss, parting her lips a little more to grant him access. His taste fills her mouth, it’s minty fresh, and her arms move up to lock behind his head, fingers thread through his short hair. He pulls her tighter towards him, melting his body to hers. She can feel his heart beating against her chest. His hands move down her back, until he grabs a handful of her ass.

“Okay, we got it!” Someone shouts and that’s the cue to stop. That’s the jerk that pulled them back to reality.

They part but Dean leaves his hand on her waist. When she looks at him, she can see the pink in his cheek, the red of his lips. She probably doesn’t look any different. Her hands go up to his lips, brushes away at them to clean them from excess wetness and he does the same for her, fingertips ghosting over her lips and it takes everything for her not to suck them in and make the situation awkward.

“If you two lovebirds could give us room for the next guest?” A woman wearing a headset comes and leads them towards the entrance. 

The moment is over.

They sit down at their table and it seems like Dean knows everyone here. He introduces her as his wife and she shakes more hands than she ever has in her lifetime.

When the meal comes, she complains about the too tiny portion, which prompts Dean to laugh out loud, saying it’s a relief that finally someone voices their opinion. He can’t stop laughing even if it isn’t even that funny? She hasn’t eaten and this is just making her grumpy.

“Dean, people are staring,” She says as one woman at their table clears her throat audibly.

Dean’s laughter dies down after her warning and he leans closer to whisper to her, “I don’t really care about those people. Can you hold on a little longer? There’s going to be dessert and if you’re still hungry, we can go and grab something on the way home, okay?”

“Okay,” She says, picks at her food and in two mouthful, it is already gone.

“Hello Dean,” A voice makes both of them turn around.

“Hey, Crowley,” Dean greets the man, stands up to shake his hand so she gets up as well. 

Crowley smiles, stares at her and back to Dean, “Another month, another woman, I see?”

“Oh,” Dean shakes his head, chuckles softly, “This one stays. I put a ring on her.”

“Did you? Lovely! Congratulations!” 

Y/N gives the men space to talk business and excuses herself to go to the bathroom. 

When she walks out, Dean’s waiting right outside, back leaning against the wall. 

“What are you doing here?” She asks and Dean grins when he sees her, pulls her to the side and walks with her a couple of feet away where nobody could see.

“Look, I’m sorry about Crowley,” He apologizes and she has to frown because she doesn’t know what he’s talking about. Dean sighs, “The comment? You know? The woman of the month?”

“Oh,”

“I don’t want you to thin—”

“—Dean, it doesn’t matter what I think.” She interrupts him. Of course she knows about the women. She sometimes has to buy them flowers or book tables at restaurants. She’s not an idiot. Dean’s good looking and he’s single, he has the right to date around, “You're notorious for having a different girl on your arm all the time. You think I don’t already know that? I’m your assistant, believe me, I know.”

“It may be true that I take them out to social gatherings but it doesn’t mean that I’m fucking all of them.” Dean hisses, and she knows that he wants to keep his voice down.

She cocks an eyebrow and grins, “So, only some of them then.”

“Jesus,” Dean rubs over his scruff.

“I don’t know what you’re trying to tell me,” She says, and adds, “Do we need to go over a story so that we’re telling the same one?”

“Maybe we should,” Dean says and he places his hand around her waist, pulls her further away from the gathering until they are standing in a hallway next to the kitchen. She stands with her back against the wall while Dean crowds her in, shielding her from prying eyes.

“What do you say when someone asks how you fell for me?” She asks him, and she doesn’t know why her heart’s beating so fast.

Dean looks at her then, his gaze is intense, it makes something flutter in her stomach. His thumb comes up to brush against her bottom lip, “Your smile. You have a beautiful smile.”

She has to swallow hard at that, “And how did I fall for you?” 

Dean chuckles, leans down a little more, his lips ghosting over hers, “I can be persistent. I came to your work and showed up every day until you said yes. It’s not even a lie,” he kisses her and it’s so soft, too. She almost has to whimper. He grins, kisses her again, equally soft and gentle. 

He’s still grinning when he parts, “Come on, let’s go to the bar.”

Taking her hand, he pulls her away to the front again, and leads her towards the bar.

“But dessert,” She says, a little disappointed that she’ll miss it.

Dean laughs and places his hand around her waist, pulls her close and kisses her temple, “I think it’s going to be some weird marzipan shit anyway. It’s not worth it. I’ll feed you when this is all over, okay?”

Y/N sighs and rolls her eyes, “Fine!”

He grins at that, pulls her closer to kiss her cheek, “That’s my girl— oh no!” His grip tightens on her hips.

“What?” She tilts her head to ask him and notices his lips pressed into a thin line. When she looks back ahead, she sees what he is looking at.

He is looking at them.

Chuck and Amara.

“Did you know they were going to be here?” She asks curiously.

“No, I didn’t.” He hisses through gritted teeth.

“Dean!” Chuck greets his new business partner.

“Chuck,” Dean says, tries to stay professional and then he turns to the woman and nods at her, “Amara.” Dean clears his throat, “This is my wife, Y/N.”

She holds out her hand and Chuck takes it, lowers his face to kiss the back of it, “I thought he was just making shit up,” Chuck chuckles, “But look at you, you’re real. It’s nice meeting you, Y/N.”

When she holds out her hand to Amara, the woman doesn’t even acknowledge her. Her lips are thin. “Your marriage is fucking fake Dean, and you know it!”

Y/N’s jaw drops, “Excuse me?”

“Oh, please,” Amara turns to her, “We all know that he’s not married! And now suddenly he has a wife? I am his wife!”

“I—” She starts to speak.

“—Don’t you dare talk to my wife like that.” Dean’s loud, it makes everyone around him flinch. And then he hisses, “I don’t even know what happened alright? All I know is that I woke up the next day with a marriage certificate propped up on my fucking nightstand.”

“Don’t think you can get away with it, Dean,” Amara’s fuming, Y/N can tell, “My lawyer is talking to Sam. He’s still waiting for that court date to annul our marriage, isn’t he? I’m sorry to say but if you want out, I want more money or else I’ll sue. And I’ll win.” Amara storms off before she or Dean can say more.

Chuck stays, though. He keeps his cool. “Don’t mind her,” Chuck says, “She’s just not used to not getting the things she wants. I’m on your side. If you’ll excuse me,” Chuck pushes himself away from the bar to greet someone else but not without turning back before he leaves, “We’re still on for that dinner?”

“Yeah, we are.” Dean says, lifts his hand for a salute.

“Wow,” She turns to the bar and the bartender comes around and asks her what she would like, “Do you have shots of tequila?”

The bartender nods with a smile. 

“Then two please.” She holds out two fingers and Dean raises his eyebrows to which she just shrugs.

The shots are placed in front of her and Dean reaches out for one which makes her swat at his hand. 

“Hey!”

She chuckles, “Who said they were for you? Get your own drink!”

Dean laughs, loud and sharp. “You’re something else, you know that?” He kisses her temple before he orders a whiskey and watches her drink her two shots.

“What did Chuck mean by he’s on our side?” She asks Dean and he sips his glass.

“Chuck wants Amara out. He just doesn’t have the money to buy her shares from her. He’s about to do anything that would get her to hand over the shares to a reasonable price but she wants double for it.” Dean says in a low voice, “That’s why he was on board when I showed interest. He wants to slowly push Amara out.”

“She sounds greedy,”

“That’s because she is.”

  
  
  
  


*

  
  
  
  


Meeting Amara kind of put a damper on the evening that has started more than alright. They’re sitting in the limousine, neither of them talking for a long while. It’s Dean who breaks the silence first. 

“Are you still hungry?”

“Ugh, I kind of lost my appetite.” She sighs.

“Yeah, that happens every time I see Amara,” Dean chuckles tiredly. 

They return to silence. She’s looking out the window, and starts to count passing streetlights to pass the time and silence.

“Penny for your thoughts,” Dean says after a while.

Looking at him, she sees him smiling at her softly. How he can still manage to smile is beyond her. 

“Aren’t you scared that she’ll get what she wants?” 

“Is that why you’re so upset?” 

“Duh!”

“Hey,” Dean’s hand finds hers, he squeezes it, “Don’t worry about it, okay? We just keep on doing what we do. Sammy is good at what he does. All Amara has are empty threats, she’s got nothing on us.”

_ Us. _

He says it so easily. It might be weird but she likes the sound of it.

Dean leaves his hand on hers the whole way back and takes it again when they get out of the limo and ride the elevator up in silence. 

Once inside, he lets go of her and that’s okay and not okay at the same time. She’s confused and she doesn’t even know why. All she knows is that she feels things she shouldn’t.

“I’m going to bed,” She says and he probably will too, because tomorrow is a work day and it’s already late.

“Okay,” Dean takes a step closer to her, reaches out to touch her, fingertips ghosting over her arm, “You did great today. I haven’t had that much fun at an event for a long time.” 

“It was my pleasure,” She replies, smiles a tired smile.

Dean takes another step closer and he’s so close again. She tries not to think about their kiss but that’s impossible because it’s the only thing she can think about right now. He weaves both his arms around her waist, pulls her closer and places a kiss on her forehead, “Good night, Y/N.”

She nods, and takes a step away from him, keeps her head down to hide the fact that she’s beet red, and walks to her room with an extra sway of her hips (just because she can). She turns around at the corner to see him smirking at her. 


	5. CH05

Y/N wakes up late the next day. It’s probably because she tossed and turned in her bed for quite a long time. She couldn’t sleep, her mind constantly on Dean, thinking of that damn fucking kiss and his gestures of affection. Even though it was the last thing she wanted to think about. After about two hours of lying awake, she decided to do something about her sexual frustrations. 

Of course she had thought about going over to his room but that would mean that she might have to cross a line she doesn’t know if she’s supposed to be crossing. Although she’d think that Dean probably wouldn’t mind? She just doesn’t know? He’s so hard to read. Either that or she’s too oblivious to notice these kinds of things. 

So, she lay there in the dark rubbing herself, and however much she wanted to come, it didn’t work, and that frustrated her even more. She thinks she fell asleep angrily, if that’s even possible.

She stretches in bed, pulls the cover over her head again and tries to fall asleep one more time. There’s still that stupid tingling sensation between her thighs and it gets more unbearable the longer she’s awake. That’s just fucking great. 

When it becomes too unbearable to stay in bed much longer, she gets up and reaches to the night stand for her phone. As soon as the lock screen lights up, she sees a text from Jack. 

_ J: [picture] _

She thumbs the message open to look at the picture, it’s one of her and Dean from last night. They really do look like a happy couple. 

_ J: Do you wanna tell me what’s that all about? When did you get married and why didn’t you tell me? _

_ Oh, no.  _ She totally forgot about the pictures that hit the internet this morning. Well, she thought about it but it’s not like Dean’s an A-list celebrity so she never really thought that Jack’s going to find out about it. Apparently, the joke’s on her.

_ Y/N: I’ll explain everything to you soon, alright? Just trust me.  _

She doesn’t wait for a reply, she needs coffee in her system first if Jack should answer, but knowing him, he probably won’t. He’ll give her the silent treatment for at least two days. She walks out into the living area in only her sleep shirt because she’s getting bolder around here, and also mainly because she knows that Dean’s already out at work anyway.

Today, she thinks that she’s going to need to hit the gym. Needs to somehow get her frustrations out, and then she’ll let the massage comforter knead the tension out of her. Maybe then she’ll be able to sleep again. She might take an afternoon nap after, for good measure.

Walking into the kitchen, the familiar smell of cologne and coffee greets her and there’s another sticky note on the coffee machine.

_ I hope you slept well. Thank you for coming along last night. I meant it when I said that I had fun. Don’t overthink the thing with Amara, okay? I want you to relax today. I’ll see you this evening. — D _

She shouldn’t be smiling. Why is she smiling? 

_ Ugh, Dean. _

_ Ugh. _

Yeah, she definitely needs to hit the gym.

  
  
  


*

  
  
  


When she’s changed into her gym gear, her phone pings with a message.

_ G: You need anything? What are you up to? Gabe _

She frowns a little. Gabe? Why is he texting her? She doesn’t have time to think so she quickly types in a reply.

_ Y/N: No, thank you. About to hit the gym now. _

Crouching down, she ties her shoes and searches for her headphones. It takes her an awfully long time to find them, as she couldn’t for the love of her remember where she put it. By the time she finds it, she’s already sweating bullets.

She runs to the front door and when she opens it, she bumps right into Gabe. Something falls out of his hand from the impact and drops onto the floor. Her eyes go from Gabe to the  _ thing _ .

“Oh, I thought you were out, sorry.” He gets back on his feet, quickly picks up the package from the floor and hides it behind his back.

If he thinks that she didn’t see it, he better think again. Because it’s a fairly large packet of condoms (fucking condoms!) and she couldn’t have missed that if she tried.

“Who are they for?” She asks, and feels something squeezing at her heart. Something that makes her chest hurt.

“For me,” Gabe answers quickly.

Y/N stares him down, raises her eyebrow. She could ask him if they were for him, what he’s doing with them here. Or why he comes in when he thinks that she’s out. She could voice all of her thoughts but instead, she gave him a silent glare, and crossed her arms over her chest.

Gabe sighs and rolls his eyes before he speaks, “Fine, the boss said to come in when you’re out and drop it in his room.”

So it is for Dean! Just like she thought it would be.

“You can take it back,” 

“But—”

“He doesn’t need them.” She hisses, and cuts Gabe’s sentence short.

“Fine. Okay, but you are going to explain to him why I couldn’t drop them off.”

“Gabe, just go.” She does her best to stay calm but on the inside, she’s raging.

She watches Gabe lower his head and retreat. After she’s sure that Gabe’s gone, she sends Dean a text because she doesn’t know his schedule and doesn’t want to interrupt one of his meetings. Plus, it’s easier to do it by text because right now, she doesn’t even want to talk to him at all.

_ Y/N: CONDOMS! Condoms, Dean? Really? We had a fucking deal. I’m out! _

Gym is cancelled. She needs to get out of here fast and storms back into the apartment and hurries to her room. She takes out her suitcases and starts to pack. Her phone chimes a couple of times but she ignores it. 

One full suitcase later, she hears him. 

_ Fuck! _

She was kind of hoping that he’d be in a meeting and couldn’t get out of it. Or maybe, in hindsight, she should have sent the text after she left but she was too fucking mad to think straight.

The front door slams so loud, it makes her jump, and his dress shoes click away on the marble flooring. They come closer and there’s nowhere for her to hide but in this room. 

“Y/N!” There’s a knock, “Open up!”

“No!”

“Jesus, you know that I could just kick the door in, right? So open up now or I will.”

_ Ugh.  _ Would Dean really kick the door in just to talk with her? She decides not to test that theory. Besides, what could go wrong, right? She’s still mad and running away from problems won’t make it go away. She’d tried that one, but it didn't work.

She walks to the door and opens up to a distressed Dean. His tie’s a little loose, his hair ruffled up and he’s sweating. She can see the little droplets by his hairline. 

“What the fuck happend?” He growls at her, it’s low and deep and it should maybe scare her but she’s unfazed. Had seen him like this more time than she can count.

“ _ You _ ask me what happened? Gabe brought you a pack of condoms, Dean! That’s what happened! Condoms! A fucking big pack, too!” 

Y/N throws her hands in the air, her throat makes a frustrating sound. And then she tries to breath to calm herself while Dean’s still staring at her, one fucking eyebrow raised. 

She ignores him and goes on, “Fucking condoms! When we both agreed that we’ll stay abstinent and won’t flirt or fuck anyone else in the six months so as to not jeopardize this whole fucking fake marriage!”

“Jesus Christ,” Dean breathes out, threads his hand through his hair, “That’s what you’re upset about?” 

He talks like it’s no fucking big deal! It makes her even more mad. 

“Of course I’m fucking upset! I’m pissed!” She spits out her words, “You let him bring you condoms so you can fuck around? How’s that fucking fair to me? All eyes are on me, Dean! If I slip, I’ll take you down with me, but if you sleep around, that’s o-fucking-kay? You’re a fucking hypocrite!” She notices that he steps in some more but there’s room by the door so storms past him, knows that one of her books is still in the living room and she wants to grab that now because she can’t stand there and look at him one minute longer.

“Y/N, calm down, let me explain,” He talks in a calmer voice, and follows her. Damn his fucking long legs because he catches up to her and grabs her arm, makes her turn and crowds her against the wall, one hand placed right next to her head and one hand on her hips, holding her there, “Please.”

He wants to explain? Yeah, sure. She’s looking up at him, challenges him, a frown etched deep in her face, “Explain? What is there to fucking expla—”

She can’t finish her sentence because Dean attacks her mouth and kisses her roughly to shut her up. And why is she giving in? She shouldn’t be giving in but fuck, if his kisses doesn’t make her weak in the knees. 

He leaves his forehead on hers when he parts, pecks her lips once more when he sees that all the fight has left her body. Dean sighs before he talks, his voice is deep, gravelly, “Goddamnit, Y/N, the condoms were for us, alright?”

_ What? _

“For us?” She frowns and Dean chuckles, his breath hot against her face. Coffee and chewing gum. He’s a notorious gum chewer. It sometimes drives her nuts because she has to make sure that there is gum everywhere in the office should he need one.

“Yeah, I was to make you a proposition. If we’re not allowed to date and see other people, I was gonna ask you if you’d be game if we—” He points his index finger between the two of them, “—you know, enjoy each other. No strings attached other than the fake marriage,”

“You want me?” She doesn’t believe him and he knows that she doesn’t. His mouth seals around hers again. It’s a little rougher, harder, his hot tongue sliding against hers, both of his hands are on her hips, fingers digging into her flesh. Before it can get too hot, he breaks it off and she whimpers against his mouth, making him chuckle.

“You just don’t see it, do you?”

“See what?”

“My god, Y/N! You turn me on so fucking much, you have no fucking idea.” His face changes. His eyes are a little darker, his voice a little deeper, “The first night with you? I was so hard I jerked myself off in the showers.”

Her mouth opens to form an ‘o’, “‘S that why you didn’t wanna get into the tub with me?”

He lets out a breath, “Yeah, I didn’t think I could have hidden my boner and it was for your own safety because I might have just attacked you.”

She grins.

Dean chuckles nervously, it’s rare that he’s nervous, “And last night? Last night was super hard because I couldn’t sleep. Every time I closed my eyes I thought about you and how you tasted. How you’re just laying in the next room. I had to take another long shower, thought of you when I did it.”

Y/N has to chuckle at the image and it makes her light headed. He thought of her? 

“So,” Dean says, pecks her lips again, “What do you say? You game? While you’re here we could have some fun?”

Y/N lets his words sink in. 

While she’s here they could have some fun. Yeah, they could. She’s clearly attracted to him, and he might be to her either. They’re adults, right? Sex works without feelings, you don’t have to love someone to have great sex, right? 

She stands on her tiptoes, hooks her arms around his necks and looks at him. He has a frown on his face, and he looks at her expectantly. 

And when she nods, Dean smiles, crashes his mouth on hers, kisses her wantonly, teeth biting down on her bottom lips, making her yelp up into his mouth. 

Dean pins her to the wall, presses his body closer, his hand goes from her hips to behind her back to knead at her ass and she arches her back, giving him better access. She can feel that he’s hard right now.

“Jesus, fuck—,” Dean pants, “I’m so hard I could pound nails.” He thrusts his hips, and it gives her just the right friction. 

Y/N giggles against his lips and Dean shuts her up with a bruising kiss. His hands go back to her hips, turns her around roughly and she braces her hand on the walls to soften the impact. His mouth kisses her cheeks, goes down her jawline and nibbles at her throat and she arches her back, drives her ass into his bulge while his fingers dig into the seam of her yoga pants at her ass, tearing the fabric in two.

“Dean!”

“I’ll buy you new ones,” His lips suck at her pulse point, tongue wet and hot on her skin, tears some more so that her pants are hanging down her legs, only now held together by the elastic band around her waist.

His long fingers move her string aside, strokes along the crack of her ass to the front, groans when he feels that she’s soaked there. 

“Fuck,” She curses and arches her back some more. It feels so good to have someone else touching her there other than herself. 

Dean groans when he feels that she’s soaked, and he whispers into her neck, “Can— can I fuck you? I don’t think I can sit through a meeting knowing that you’re going to be here. All ready and fucking wet for me.”

God, his words turn her on so much.

“Ye-ah,” Her breathing hitches, because he slips in a finger and he groans out some more at that.

Dean sucks in her skin on her neck, lets it go with a huff of breath and a grin and pulls his finger out. He has to chuckle when he hears her whimper at the loss. He takes a step further away and she hears the metal of his belt buckle. She stays pinned there, doesn’t dare to move but she wriggles her ass and it might make her look needy, which she really is. 

She hears a hiss when Dean frees his cock, can hear him spit into his hands and he’s probably working his own dick and god, she wants to see. 

“Look at you, fuck—” He comes closer, his hand squeezing her ass, fingers spanning wide. He spanks down on them too, making her yelp up and then he threads his fingers through her folds ones more before she hears shuffling behind her, and there’s his fucking tongue at her center, his nose buried deep into the crack of her ass. 

“Oh fuck,” She lets out a huff of breath and lowers her forehead to the cold wall. And she can’t help it, she has to arch her back, pushing her ass into Dean’s face and he hums, while his tongue twirls around her entrance. She hears the wet sound of Dean working his own dick while he licks into her.

“You taste so fucking good,” He mumbles, licks another broad stripe, slurps up her juice and she keens above him.

After a while he comes up again, kisses from her shoulder up her neck, his mouth is wet. His hard cock rests between her ass cheeks and he thrust his hips, can’t not stay still, cursing under his breath, “Fuck, I don’t have any condoms because you sent Gabe away.”

“Don’t care,” She manages to say and she’s fucking needy, she doesn’t care anymore because she feels his heavy and hard dick between her cheeks and she wants it inside.

“You sure?” 

“Fuck me already,” She drives her ass back, wriggles with it and Dean has to chuckle. 

He takes his dick into his hand, threads the tip through her slick and rests it at the entrance of her cunt. Dean lowers his head to her throat, sucks on a patch of skin before he pushes in. 

“Oh shit,” She moans out, throws her head back a little and Dean drives his teeth into her throat at the feeling and holds her skin between his teeth as he dives in further.

Dean goes in agonizing slow, but she needs that, needs time to adjust and to accommodate his girth. He's big, at least bigger than the dicks she had, which aren’t really many, but that’s not the point. He works his way inside and she stretches around him, helps him by moving her hips to make it easier. Dean groans out when he’s sheathed all the way inside.

“God you’re so deep,” She grits her teeth.

Dean’s panting hard and he kisses a way up her throat until he kisses the sensitive skin below her ear, he doesn’t move just yet. “You okay?” He whispers.

“Yeah,” She says, has to take another deep breath, “Yeah. Are you?”

“‘M trying not to come. You feel so good, fuck—” He hisses and then he composes himself, “When was the last time you done this?” His hip starts to move slowly, fucking up into her as deep as he can go and moves out far enough to just leave the tip in, only to repeat his movements. His hands are all over her, up below her shirt to knead at her tits through her sport bra, on her hips, around her waist, on her ass as he spanks her twice and spreads her wide to watch his dick going in and out of her cunt.

“God, I don’t know, maybe six months ago? Why?” She doesn’t really understand why they’re talking about this. She can’t really concentrate with his dick making her feel so fucking good.

“It feels like you’ve never done this before, you’re so goddamn tight, Jesus! Tightest little pussy,” His hands fists in her hair, yanks her head back so he can whisper into her ear, “You like my cock, huh?”

“Uh-huh,” She manages to say, his other hand is on her throat.

“Uh-huh?” Dean whispers, “Look at you taking my dick like a good girl,”

Fuck, he’s talks so dirty and it turns her on so much. She’s grinning, enjoys the feel of him pounding into her. Dean moves faster now, fucks the laugh right off her face.

After a while he lets go of her hair, pushes her against the wall once more and his mouth is always on her, nibbling, kissing and sucking the skin of her cheek, throat, the back of her neck. He fucks her deep, hard, she’s going to be sore, she just knows it. But it’s good. So fucking good because his cock curves at the tip, it rubs at her spot on the inside and she’s so fucking close. 

“Dean, I’m— I—” Shit, she can’t even say anything coherent. Her nails dig into the wall.

“Come for me, baby,” He nibbles down her jaw, sucks at her pulse point once more, one of his hands sneaks around the front, rubs along her clit.

_ Baby. _

That does it. 

She shakes around him and her pussy squeezes and pushes at his dick so hard it slips right out, but Dean grabs it and pushes it right back in to fuck her through her orgasm.

“Good girl,” Dean pants, his thrust starts to falter right after, “Baby, where do you want me to come?” 

“Come in me,” She whispers, “I want you to come deep in me,”

“Jesus fuck,” He bites down her shoulder and holds his breath as he buries himself balls deep inside of her. He’s trembling, his hips jerk.

He breathes through his nose, his mouth still on skin, and he shudders. Dean sucks at the skin that bears his bite mark, soothes it with his warm tongue. “Jesus, I couldn’t even warn you. You saying things like that made me explode.”

She chuckles, her hand goes up to cup at his cheek, she can feel the prickle of his scruff.

“Shit,” Dean lowers his forehead to her shoulder, and she scratches at the short hair on the back of his head, “I have to go back to the meeting I kinda left in a hurry.”

“You left a meeting?” She frowns, “An important one?”

“Kinda? Donatello was about to present me with the numbers of the west coast. I gave them a thirty minutes break,” He chuckles, “I ran here. Couldn’t risk you leaving.”

“Jesus Christ, Dean, go back, now!”

“I am,” He growls and pulls himself upright. It also means that he’s slipping out of her and she squirms at the empty feeling, hates it already.

Dean’s cum drips to the floor and she turns around, still leaning against the wall because she doesn’t know if her legs will be able to hold her up. There’s cum splatters between them and she can see that while Dean tucks himself in, he’s looking on the floor, hesitant about cleaning it up and knowing that he’ll show up even later if he does it.

“Go! I got this!” She tells and Dean nods at her, zips up his pants. While he is securing his belt, she helps him right his tie. 

“I’ll smell like sex.” Dean smirks.

“Just run back, then you’ll smell of sweat.”

He snorts out a laugh, “Right, we’re good?”

“Yeah,”

He raises his eyebrows as if he doesn’t believe her, “You’re not leaving?”

“Nu-uh,” 

How can she? How is she supposed to leave now? Now that she knows that it was all for her?

Dean smiles, grabs her by the waist to pull her close, his fingers skim over the bite mark on her shoulder, “‘M sorry bout that,” 

Y/N shakes her head, “It’s okay, don’t worry about it.”

He smiles and leaves a last lingering kiss, “I’ll see you later, okay?”

She nods and watches him leave. Her pussy’s still pulsing and she feels hot and wet, Dean’s cum is running down her legs when she walks to the kitchen, leaving a trail behind. 

Well, there goes her workout, instead she'll get on all fours and clean up the mess they made. 

After she cleans up, she sits in the hallway, right at the very spot that Dean just fucked her and leans her head back and closes her eyes. 

_ Oh my god _ , she just fucked her boss, or more like, he just fucked her! If that isn’t fucked up, she doesn’t know what is.


	6. CH06

After her shower, Y/N looks at herself in the mirror, sees her throat pink from all of Dean’s kissing and sucking. He was rough but also careful not to leave a mark that would stay. Except for that bite mark. It’s still red and she can clearly see the outline of his teeth. 

_ Oh god _ , Dean. 

He’s her boss.

She has had sex with her fucking boss!

Y/N still can’t believe it and has to chuckle and bite down on her lip as she moisturizes the mark and gets dressed. Thinking about going for a walk in the park before she might get into the hot tub to help soothes her sore body. 

  
  


***

  
  


Y/N sits in the tub, squints her eyes and wrinkles her nose at the soreness she feels. It definitely has been too long since she last had sex and her body is just really not used to it anymore. It doesn’t help that Dean’s rather big. 

Ugh. Dean.

Her boss, Dean.

The bossman, Dean.

She really did it, right? She really agreed to be friends with benefits, didn’t she? She was so fucking horny and turned on, she would have agreed to anything probably. 

But thinking back it can’t really be bad, since the sexual frustrations were killing her. So it’s a win-win for both of them, right? She wishes Ruby was here but she’s probably still working and Y/N doesn’t want to disturb her at work. Somehow she wishes that she was still working too. This stay at home and be a trophy wife thing really isn’t for her.

Y/N opens up a page to her book in a tub, she still has some time to kill before Dean would get back. It’s not even 5pm yet. However, she gets interrupted when she hears the door and a familiar voice calling out for her. She cringes some more then, feel embarrassed that she’s in the hot tub again. He’ll probably think that’s the only thing she does here. But it’s really the little things she finds comfort in, and she knows that she shouldn’t be ashamed but still, she is, which is ridiculous.

“Enjoying the view?” Dean emerges out of the penthouse and leans his body against the frame of the terrace door. He has already shrugged off his shirt jacket, the tie’s gone and his sleeves are rolled up. The muscles of his forearm move as he works on unbuttoning his dress shirt.

“Yeah,” She replies, shy all of a sudden. But how can she not be, she’s been thinking back to what they did. 

Dean grins smugly as he watches the color in her cheeks rise, “I’m enjoying my view, too.” He walks over, still unbuttoning his shirt and she can see his broad naked chest. It’s freckled, too. She wants to connect them with her tongue. 

He leans in, kisses the top of her head, “You okay?”

It seems so easy. He’s totally chilled about it. She doesn’t understand.

“Y-yeah,” 

Dean braces his hands on the ledge of the tub, his shirt falls open, she can see his body now. He’s firm, defined and soft. There’s a little happy trail leading down from his navel, it disappears inside his pants, and she’d like to take that trail, see how happy it can make her again. 

_ Oh god, focus, Y/N! _

“I was thinking of taking a shower and then we’ll go to the pharmacy.”

There’s a lift of her eyebrows, “Why?”

He reaches one of his hands out to tuck a strand of loose hair behind her ear, “Because I shouldn’t have let myself be carried away and come inside you.”

Y/N couldn’t help but grin.

“Why are you grinning?” Dean asks with a frown.

“It’s okay, Dean, I’m taking the pill.”

“You are?”

She nods, “Yeah.”

He’s looking at her, his eyes skims over her face and she sees it, sees it in his face that there’s a question burning on his tongue. Maybe something along the line on why she’s taking the pill when she’s hasn’t been in a relationship for over a year, because she’s sure that he did some research with Ruby. He’s so difficult to read, it frustrates her. 

Instead of asking, his face changes, it’s softer now. Perhaps he thinks that it’s too personal and it’s not his place to ask, and after a long while, he smiles, “In that case, mind if I join you?” 

“Sure?” It shouldn’t have come out as a question, she doesn’t know what’s happening with her.

“Good,” He grins and winks before he disappears inside.

Just when she begins to wonder what’s going on, Dean reappears with a bottle of wine and two glasses. He’s still dressed, though. He places the glasses on the little table set up next to the tub, fills both glasses and sets the bottle back down wordlessly.

There’s a grin on his face when he looks back at her, it’s all cocky and bravado. His eyes are on her as he takes a step back and starts to strip out of his clothes. Dropping each item in what seems like slow motion.

“Dean, someone could see you,” She hisses, her cheeks burning bright.

“Relax, nobody can see.” He says and looks around, “Unless there’s a drone or a helicopter somewhere, which we would hear.”

He is abso-fucking-lutely so chilled about it, it baffles her.

After a while of stripping, Dean’s standing naked before her, and he has absolutely no shame. She admires that a little? Because she’s shy and she could never do that. Not with someone she basically just started to get intimate with. 

Y/N tries not to look at his cock. Which is big, and oh god, she had that inside of her. 

Dean starts to chuckle, can probably read her face like an open book. He steps closer, gets in and sits on the bench in the tub next to her before he twists his body to reach for the glasses, holds one out for her.

She takes it and they clink glasses before she takes a sip. It’s good, she feels the wine travel down her throat.

“We can just talk, no pressure, alright?” Dean says and sets his glass down. He moves just a little closer, his hand rubs at her thigh, “I feel like I wanna get to know you better, you can ask me anything you want. I want you to feel comfortable around me, okay?”

“I  _ am  _ comfortable around you,” She says, which prompts Dean to snort out a laugh. 

“Liar,” He mumbles, moves in and holds out his wet hand, cradles her face with it and pulls her in for a kiss. Tongue teasing along her bottom lip, but before she can even open her lips to let him in, he breaks the kiss, “See? You’re all tense.”

How does he know?

“It’s your brother, isn’t it?” Dean asks and her jaw drops.

“How?” She takes another sip of wine, mainly to conceal her irritation of Dean knowing what she’s thinking.

He has to chuckle at that, “He called the office today, Ruby picked up. He demanded to speak to his sister’s husband.”

She almost snorts out the wine she still has in her mouth, “He did not!”

“Duh,” Dean grins.

“Oh, no! I’m so sorry.” She feels the red of her cheeks spread over to her ears, “Did you talk to him?”

Dean drinks up his glass, places it back on the little table on the ledge, “Not right then. I was in a meeting,”

“Thank god,” She mumbles more to herself than Dean.

He laughs, moves closer, his thigh is touching hers. He is back to stroking it too, getting higher up with each stroke, “But I called him back.”

_ Shit _ , Y/N bites her lips, “What did he say?”

“He said he texted you and you didn’t answer his question, and that’s why he asked me. Said if I hurt you he’ll, and I quote,  _ rip my fucking lungs out _ .”

_ For fuck’s sake, Jack! _

“It does sound like him,” She smiles warily, “What did you say?”

Dean leans closer, nuzzles his nose against her cheek, moving closer to her nose, his hand comes up to cup her chin, tilts her face towards him. He kisses her, it’s soft and gentle, tongue teasing at her bottom lip again, licks over her bottom teeth of her parted lips. The touch of her tongue on his is electrifying, “Said he didn’t have to be worried. That I have no intentions of hurting you. At least not deliberately. And if I should, he’s allowed to punch me.”

“Be careful, Jack might just do that. He doesn’t care if you're bigger and stronger.” 

He chuckles, “Yeah, I know, he told me that he’ll keep a close eye on me.”

She groans, “I’m sorry, but Jack’s always been protective.”

“And that’s okay, really. I asked him if he wanted to come over so we could talk and explain everything to him but he said that he’s away at college and you wouldn’t give him extra money to come home.”

“Yeah,” She says, “He’s right. His only job is to stay in college, do well, and be happy.”

“I noticed that throughout our call.” Dean huffs out a breath, “Is that true? You’re supporting him through college?”

She nods, “I was so glad you offered me the job a year ago. And I’m surprised that I made it this far. Jack only has two years left until he’d graduate.”

He frowns a little, “What do you mean you made it this far?” 

Y/N raises her eyebrows, “You’re kidding, right?”

“Do I look like I’m kidding?” He frowns some more.

“Dean, every time I saw you, you were grumpy. I don’t think I’ve seen you smile at work, at least not much. If I could get one smile out of you in one week, I could consider myself lucky.” 

“Oh, come on! I’m not that bad!”

She grins, “That’s right, you’re even worse.”

“What?!”

“You’re firing people all the time. Hannah from HR has to work overtime just to get new people on board. By the way, you might want to rethink employing someone else to help Hannah. Like, I don’t know? You’re very strict but I see that it’s because you put everything into it and you want for the company to be successful, it’s just, maybe you can relax a little?”

“I am relaxed!” Dean whines and she has to laugh at that.

“Are you, really?” She asks him with one raised eyebrow, skims her fingertips over his thighs, moves up and down slowly while she watches him. Dean swallows, and his body jerks when the nail of her index finger brushes along the length of his dick, before she holds him in the palm of her hand. He’s hard, his cock heavy in her grip. Her hands can barely grip around his base. She still can’t believe that it fitted inside her. Looking down, she watches her own hand massaging his shaft and she has to bite down on her bottom lip because she’s turned on too but she’s still sore.

When she looks up again, Dean crashes his mouth onto hers, kisses her rough and deep, sloppy and wet and it’s so good? She’s craving more. 

He breaks the kiss, mumbles against her mouth, “Lose your bottoms,”

“I-I’m,” She pauses, wondering if she should tell him that she’s still sore, that it’s not a good idea if he fucks her and really she just wanted to tease him but she realizes that she’s gone too far and that she’s sorry about it.

“Don’t worry,” Dean pecks her lips, as if he just read her mind. Seriously, how does he do that? “I won’t fuck you. I can imagine that you’re sore.”

Y/N lets out a huff of breath, feels relief that he knows. She shimmies herself out of her bikini bottoms anyway, wondering what Dean’s going to do. When she gets it off her leg, Dean grabs the leg that’s closest to him and drapes it over his thighs, spreading her. 

“Let’s see how relaxed  _ you _ are,” He grins and kisses her while his hand cups her crotch. He groans into her mouth upon feeling that she’s pretty damn slick down there and it’s definitely not the water, “Still a little tense,” He smirks.

She smiles and picks up the stroking of his shaft, twisting her wrist around the head of his dick, and Dean pulls her even closer by one of her thighs, lifts her up. She weighs nothing in the water. One of her ass cheeks is half on top of his thigh and Dean massages her clit gently, threads his finger through her folds before he slides two of his thick fingers in. His movements are slow and gentle, a stark contrast to how he fucked her earlier.

Dean moans into her mouth, sucks at her tongue, “I just fucked you a couple of hours ago, my cum’s still in there and you’re still so goddamn tight,” His voice is raspy, he’s breathing hard.

Before she can enjoy his fingers more, he takes them out, the hand goes to her hips and he lifts her up. Manhandles her up to the ledge. She’s bare to him and it seems like she’s bare to half the world too, but strangely, she doesn’t care about them. 

“Spread your legs for me,” His voice deep, it’s a low growl and he comes to sit in between her now spread legs, she can see that he’s still stroking himself while he sprays kisses along her upper thighs. 

He nibbles and sucks at her flesh, coming closer to her core and she’s pulsing down there, her need for him to touch her almost unbearable. 

Dean spends an awfully long time just staring at her pussy and she feels a little insecure, closes her legs but he stops her, “No, let me see,” He says, his fingers go to her clit, draws gentle figure eights on it, “Prettiest little pussy,” His voice is raspy, it’s trembling a little, too.

Hooking a hand around one of her thighs, he pulls her to the edge and she can barely hold herself up. He threads through her folds one handed, still jerking himself off with the other hand and it’s so hot to know that he’s turned on by  _ this _ . That he’s turned on by  _ her _ . 

“Fuck,” He growls, lowers his head and licks up a broad stripe through her center, “I fucking love how you taste.”

She has to bite her lips so as not to moan out too loud. His tongue is massive, it’s wet and smooth and oh, god. She throws her head back as he begins to nibble at the hood of her clit and Dean chuckles, slurps up her wetness and sucks some more.

His mouth is sealed around her clit and he teases at it with his tongue. Slower at first before his tongue picks up speed and he breathes through his nose, hot air hitting her wet skin. It’s fucking hot to watch him. 

Dean licks into her with his tongue, goes deep and it feels so soft. His scruff scratching at her thighs and around her folds. 

Y/N writhes above him, can barely hold herself still and she’s damn close, “Oh god yes! Yes, yes, yes, keep going, Dean, please,” Her hand goes to his head, fingers gripping at his hair as she works her hips, rubbing her cunt against his face. 

He doesn’t seem to mind at all because he lets her pull his face into her pussy while his own hand works frantically on his own dick. She can hear a wet slurping sound that makes her blush and turns her on at the same time.

“Come, baby.” It’s only a whisper against her folds, but his lips are connected to her, and then he hums, sending vibrations to her clit and it fucking pushes her over the edge.

She comes with a shaking of her legs, her whole body trembles. There’s something inside of her exploding, and before she can even think straight, Dean pulls her down again, making her sit on his lap as he claims her mouth, seals his lips around hers, grunts and squeezes his eyes shut as his cum makes its way to the surface.

He chuckles into her mouth, pecks her lips and leaves his forehead on hers. “Guess I have to call for someone to come exchange the water,” He smiles against the corner of her mouth and she has to grin at that, “Come on,” Dean stands up, fishes her bikini bottom out and squeezes out the tub water to lay it on the ledge before he holds out his hand to help her out. 

She still can’t believe that he came just from jerking off and eating her out. Nobody’s ever done that to her. Nobody seems to be alright with just eating her out and demanding nothing else in return.

Dean cocks his eyebrows when he sees her staring at him, still lost in the memories of what just happened, but he doesn’t say anything, just scoops her up and walks her along the hallway to their rooms.

Instead of dropping her off by her room, he turns the other way, pushes the door open to his bedroom and walks her into his bathroom.

Y/N manages to catch an eyeful, sees that his bed is neatly made. The room’s kept in wooden dark colors, not white and bright like the guest bedroom. She couldn’t see more because Dean drops her into his shower and turns on the water. He kisses her again, while the shower rain washes over them.

Dean soaps her up, and she sees that he’s hard, he doesn’t say anything, though, just keeps on soaping them both up, like it’s the most natural thing to do, and rinses them out. He doesn’t talk much, leaves kisses here and there and it baffles her how easy it all feels. How comfortable he is around her, how she has the feeling that he really truly cares about her. 

He points to the mark on her shoulder, “‘M sorry. I’ll be more careful.” He lowers his face to place a kiss on the mark, leaves his lips there.

After the shower, they dry themselves off and Dean tosses her a shirt from his closet. Hits her square in the face with it and he has to laugh at that. It's a simple white shirt, too big for her but it smells like him. In fact, she smells like him from head to toe now, since he soaped her up with his body wash. 

Y/N’s about to go out and to her room to get panties but his voice is loud behind her, “Where are you going?”

“I gotta go get panties,”

He chuckles, she can feel his chest vibrating on her back, “You don’t need it,”

Dean kisses the crown of her head and picks her up, throws her over his shoulder and carries her out into the living area and drops her on the couch. She takes the blanket to cover up her lower body and Dean grins.

“What?”

He shrugs, “I kinda like the idea of you not wearing anything underneath the shirt.” He emphasizes his words with a pinch at her nipple and she gasps. He kisses her again, tucks her hair back behind her ear, “And I like seeing you in my shirt.” 

He gets up, walks out to get the glasses of wine they left there.

Her cheeks feel hot. 

And she tries. She really tries not to fall for him. It gets harder and harder with every breath she takes.


	7. CH07

Dean returns from outside, sets the glasses down and pours the wine into it. He walks into the kitchen, takes out two bottles of water and sets them on the table. “What you wanna eat tonight?” 

Y/N shrugs, she really doesn’t mind. She knows what he likes to eat and she likes the same thing too, “I don’t know, what do you wanna eat?” 

There’s a small grin on his face and it turns wider, more cocky too, and he wriggles with his eyebrows. 

_ Oh my god. _

She just walked right into that one, didn’t she?

“Jesus, Dean, I didn’t mean me!” She mumbles, rolls her eyes and Dean has to laugh out loud. 

“Well, that’s a shame because I love how you taste,” He winks, turning around to take out the delivery leaflets. 

She’s glad that he doesn’t notice the red in her cheeks.

  
  
  


*

  
  
  


They have settled for Thai and they held a stupid competition on ordering the most spicy dishes and eat it. She won, but at what cost.

The bell rings right when they both are chugging milk over the sink with tears in their eyes. Dean was already standing up straight to go to the door but he didn’t need to, because they hear the key turning in the lock and then, Sam Winchester walks right in. His eyes widen when he sees them both huddled by the sink in the kitchen.

“Uh, Am I interrupting something?” Sam asks with raised eyebrows.

“Nah,” Dean winks, “Come in.”

Sam nods, looks at them both with a grin before he walks over to the couch. They follow him after drinking a mouthful of milk.

“What is it, Sammy?” Dean asks, sits next to Sam and she makes herself comfortable on the other side of Dean, pulls the blanket over herself to hide her bare legs and pussy. 

“Just wanted to come by and give you a quick update,” Sam says. He looks from Dean to her and she can’t miss the grin on his face, “How’s it going with you guys?”

She shrugs and tries to keep a straight face, “Eh, he’s okay,”

“Hey!” Dean shouts out, “I’m more than okay, alright?” 

Sam burst out laughing, “Yeah, well, I don’t have much time to listen to you two bickering, but I have a court date. It’s going to be in a month. So everything should be over by then.” 

“Meaning?” Dean raises an eyebrow.

“Meaning that you need to live together for at least a month and afterwards you can go back to what you were. You stay married on paper for another four months after the court date and after we win, of course, and it’d be good if you can sometimes go to social events together. Just to keep up the facade.”

“Oh,” Dean says, “Yeah, that sounds good, doesn’t it, Y/N?”

He puts her right on the spot and she feels quite uncomfortable, “Yeah,” She answers. “Yeah, great.”

“Amara’s lawyer called me today, though. Said he believes that your marriage to Y/N is fake.” Sam pauses to snort out a laugh, “Well, I’ve seen the picture of the gala. Good job, both of you.” Sam eyes Dean and then her, before his gaze returns to Dean and Sam nods.

Dean shrugs but there’s a little smirk on his face, “We try.”

“Dean, you have to inform your employees that you two married in secret and kept in under wraps because you didn’t want to jeopardize your work relationship. Do they know this already? It’s important for when someone comes snooping.”

“I actually had a meeting with my staff today. Told them that we have been secretly dating for a while before we decided to take the next step.”

Her eyes widened. So they all know? She can be glad that she isn’t close to anyone else in the company other than Ruby. Otherwise there would have been questions that neither she or Dean would want to answer.

_ We decided to take the next step _ . She laughs to herself. How very business-like and not at all romantic. But that’s totally Dean. Because yeah, he sees it as another business deal and she knows that she should too.

“The lawyer also said that Amara would agree to annul the marriage if she can get 30% of your net worth.”

“SHE WHAT?!” Dean leans back on the couch, clasps his hands over his face and rubs at it. The sound of his palms rubbing over his scruff is loud in the room that just went silent after Dean’s outrage.

“Yeah,” Sam says, “But we have the upper hand in this. You guys are already married so Dean marrying again in Vegas was illegal. The court will grant us an annulment if we play our cards right. That’s why it’s crucial for us that you keep up your fake marriage and try to convince the court that what you have is real. I did my best with the documents, there’s no worry about that.”

“Well, that’s reassuring.” Dean scoffs, and Sam frowns at his brother.

She can see that Dean’s very much tired of it all.

“Anyway, I need to get going. Oh, and I have a meeting with Amara in two days. You wanna join?”

“Over my dead fucking body,” Dean hisses.

  
  
  


*

  
  
  


They settle on the couch after Sam leaves, and he hands her the remote. She zaps through the channels, settles on a movie that has already started.  _ Cocktail _ . It’s easy viewing and that’s probably just the right thing since she can’t really concentrate anyway with Dean next to her. Not when she knows how he looks underneath his clothes. Not when he’s wearing his shirt and her pussy is throbbing. He made her come twice earlier already, she should get a fucking grip. 

“Aren’t you worried?” She has to ask. She can’t not just ignore it.

He shrugs, “I’m not happy about it but I’m not worried. Not really, no.” It comes out too easy, as if he is truly not worried in the slightest, and Dean sees the frown on her face. She’s sure that he sees the pout on her lips as well. He reaches out, thumbs over her bottom lip, “Don’t worry about it, alright? I got this.” 

She nods. She really wants to believe him. She does. She’s doing this because she wants to help him — double pay aside — because Dean’s a good boss. A little short tempered but he has the company's best interest in mind. He can also read people very well and offers people opportunities to prove themselves if he sees that someone has potential. Like Donatello? He started in the company as a fucking janitor and now he’s leading a sales team. Y/N helps Dean because she wants everyone to keep their jobs and be happy, and another thing is that she really can’t stand Amara so it would be a double win if they can get rid of that bitch, too.

They watch the movie in silence for a while. It’s when she starts to yawn that Dean suggests she lays her head in his lap, and honestly, it looks inviting and the smile on his face is big, she couldn’t find it in her heart to say no to him. 

He strokes her head, when she lays down and they continue to watch but she just can’t really concentrate with Dean playing with her hair. 

“You like that movie?” Dean asks, his fingertips trailing along her jawline, which sends goosebumps throughout her body. 

“No, but I like the scenery.” It’s the truth, the movie is not really her style but they’re in Jamaica and it looks picturesque with the clear blue water and white sand.

“Have you ever been there?” 

She has to snort out a laugh at that, “No, I couldn’t afford it in a million years. But maybe one day I will be able to. Once Jack is earning his own money I can save some for myself.”

It’s silent for a long while until Dean suddenly speaks, “Maybe I’ll have a job for him once he’s done.” 

She frowns and sits up, pulls her knees to her chest. Dean’s body is still close to hers, she can feel the warmth radiating from him, “He won’t take it.” 

“And why’s that?” He raises an eyebrow.

“Because Jack would know that you’ll just do it out of pity and he’s too proud to take the offer.”

“Well, I can make him sweat for it, if it helps,” Dean has a boyish grin on his face. Something she’s never really seen on him. It makes him look younger. Makes him look relaxed. It suits him. She could get used to seeing it more often.

Y/N has no doubt that Dean is able to do that. He’s been doing that for longer than she knows him, making people sweat, that is. But it’s not for her to decide. Jack is his own person. Even though sometimes, she still thinks that he’s a little nugget and needs to be protected but he is very capable of making his own decisions. The only thing she always tells him to do though, is to own the decisions he’s making. He has to be able to live with every consequence of his decision making and so does she. Like, right now, when she feels Dean’s hand come up to pull her into him and that is because she agreed to be his wife. It’s a decision she made and she’ll deal with everything that comes with it.

“How are you feeling?” He changes the subject, probably feels that he’s invading her privacy when they talk about Jack.

“I feel good,” She smiles and leans her head on his shoulder, tilts her head up to look at him, “It’s certainly not what I was expecting,” 

Dean cocks an eyebrow, “Better or worse?”

She has to grin, “Better,”

“Good, I just wanted to make sure that you’re okay,” 

She knows that he does. He has a weird obsession with making sure that she’s okay. It has been like that since she started to work for him. Dean was grumpy and loud, yelled around a lot but at the end of the day he’d always come by and asked her if she was doing okay. The behaviour scared her at first but she somehow puts it down to some kind of OCD. He is obviously someone who likes to have control over every aspect of his life.

“Can I ask you something?” She asks and gets nervous all of a sudden.

“Anything,” Dean answers without a second thought. He didn’t even pretend to take a couple of seconds to think.

“I was going to ask you if I could have my job back?” She squints her eyes, a little afraid of his reaction and she doesn’t even look up at him, instead she keeps her head on his shoulder and looks straight into the TV.

Dean doesn’t say anything for a long time and she’s really afraid that he’ll say no. She listens to his breathing, feels his chest moving, hears his heart beating. 

“You know,” Dean sighs, “I was kind of hoping that you would want to come back.”

“You were?” She sits straight and looks at him to see that he’s grinning. So she was so worried for nothing. 

“Yeah,” He smiles, “You didn’t talk to Ruby, did you?”

“No, I was too wrapped up with— you know,  _ you  _ a-and— Jack.” 

Dean chuckles, and takes his arms from around her to rub at his scruff. He leans forward, takes a sip of water before bracing his elbows on his knees, and she follows, sits close enough to lay her face on his back. She can hear his heartbeat even better. “Yeah, uh, I was so close on firing her today but then I thought that I would be left with no assistant at all. So, yeah, you can come back.”

“Dean!” She punches his arm and he chuckles. 

Y/N can hear the vibrations of his voice. Hears it deep inside of him, and she can feel every back muscle moving. It’s so sexy, she can’t lie about it.

“In my defense—” He looks back and starts to talk, but then he stops. She rests his chin on his back. He changes the subject abruptly, probably knowing that she’ll hear it from her friend anyway, “Tomorrow you’re coming back to work as my PA because you’re my wife.”

“Your fake wife,” She adds. She needs that reminder herself. 

“My fake wife,” Dean agrees, his lips are pressed into a thin line, his dimples showing. She calls them his dimples of discontent. He does have dimples of content as well, but they are rarely seen. People in the office say that it’s a myth.

“So, your PA?” She raises an eyebrow.

“It’s the best solution. You’re my wife, I can’t let you handle other things.” 

She grins, “So you just let me handle  _ your  _ thing.” 

There’s a blush in his cheek and Dean clears his throat before his face settles on a frown.

Y/N pokes her head under his armpit with a smile. He basically holds her in a headlock, and Dean opens his arm a little more so she can fit in better. She kisses his cheek, whispers a “Thank you,” 

“You wanna call Ruby?” He asks and looks down at her, his double chin showing. He looks damn cute. 

“Nah, I’m gonna surprise her. But I’m going to bed.”

“It’s only 10pm?” 

Dean’s right. It’s not that late yet. Well, he’s probably more used to staying up late because she has a lot of meetings outside of work as well, but she isn’t used to it and honestly, her body feels tired. She can’t wait to hit that comfy mattress. 

“I have to show up on time tomorrow, my boss will be angry if I’m late. Maybe he’ll even fire me.” She makes a disgusted face.

He smirks at that, “He will fire you for being late? That sounds a little extreme.”

“Oh,” Y/N scoffs, “I’m telling you, he’s the worst. One little misstep can get you fired. I told him to change his attitude a little, and I hope that he takes my advice.”

“Has he ever treated you badly?” There’s something in Dean’s eyes. Something she can pin point as remorse. But maybe she just imagines it.

She smiles, “No, actually, he never did lash out at me. He was probably close a couple of times, though. But I’ve seen him take out his anger on others that I know try their very hardest, and that’s not fair either.”

Dean lets out a snort, “You know what? Your boss sounds like a dick.”

“He is, but I like him.” She grins, sees Dean smiling back, “Okay, I’m going to get some sleep. I’ll see you tomorrow, and thank you again.” She kisses his cheek once more, and she feels him leaning into her kiss. 

When she gets up, Dean grabs at her wrist, making her fall back on him and he manhandles her into straddling him. It takes her by surprise as well as the kiss that follows. His big palms are cradling her face, pulling her down, his tongue teases at her bottom lip, “I’ll try to change, okay? Thanks for telling me.”

“Okay,” She says, nodding and he grins, pulls her in once more. He kisses her soft and gently, tongue sliding smooth alongside hers, and she lets herself fall, weaves her arms around his neck.

Y/N’s awfully wet down there already and she can’t help but grind onto his growing bulge. His hands are on her ass cheeks, kneads them, as he pushes and pulls to help her grind on him.

Before it can get too heated, he breaks the kiss and leaves his forehead on hers, “You should go to bed, I’m not sure I can restrain myself from fucking you if you don’t go now and I know that you’re sore. So, I’d rather not hurt you.”

She can only nod, “Yeah,” She pecks his lips once more, gets up and sees that she wetted his pants, “I’m sorry about that.”

Dean stares at what she’s pointing at and lets out a soft chuckle. 

Y/N starts to walk to her room and is almost around the corner when she hears him speak. 

“‘M sorry if I was too rough. I should have controlled myself better.”

He’s talking about their quickie, she knows. 

Grinning, she turns to him, smiles bright, “Don’t worry, I like it rough,” With a wink, she walks to her room and smirks to herself because she saw Dean’s eyes widen at her comment. 


	8. CH08

The next morning, Y/N walks out of her room, dressed and ready to go to work at precisely 7.30am. She figured that she doesn’t have to get up as early as she did, because she basically lives a ten minutes walk away from the office. She’s early enough to be at the office at 8.00am and there’s still plenty of time to get a coffee into her system first. 

Opening the door of her bedroom, she catches a whiff of Dean’s cologne and takes a deep breath. She doesn’t know why, but she loves it. There aren’t a lot of men’s cologne that she likes. The boys in the office don’t smell that good and Donatello’s cologne always makes her gag. That’s why she isn’t going near him if she can avoid it. She always likes Dean’s, though.

Rounding the corner into the living space she’s surprised to see Dean standing by the kitchen island. He’s usually already in the office at this time of the morning. 

There’s a newspaper spread in front of him and he takes another sip of his coffee with a frown. When he notices her, he looks up, the frown evens out and there’s even a little smile decorating his face. She can probably count herself lucky that he’s in a good mood this morning, “Hey,”

“Why are you still here?” It’s her turn to frown because she did not expect him.

She walks over to the machine and Dean opens his mouth to speak but she pushes the button and the machine gurgles loudly. He has to chuckle and he takes another sip of his coffee, waits until the machine stops being so loud. 

When her coffee’s ready, Dean speaks, “Thought we could go in together. We’re married, remember?”

Cocking an eyebrow she looks at him, “I do, but you’re still the CEO and you have a job to do.”

“Eh,” Dean shrugs, “There’s nothing I can’t do with my phone.” He waves his phone to emphasize it. “How are you feeling?”

She drinks half her coffee in one go because she doesn’t want to keep Dean here longer than he has to be. Wants to get going, because she knows how important it is for him to be on time which is before all his other employees start. She holds her mouth when she burns her tongue, “Ow,”. Definitely shouldn’t have drank it that fast.

“What?” He frowns. 

“I just —” She pauses to trail her tongue along in her mouth, “Burned my tongue because I drank too fast.” 

Dean has to chuckle, “You really don’t have to hurry,”

Y/N frowns at him some more, “Duh, I do? You’re waiting for me and I don’t want you to be late.”

“Jesus,” Dean walks over to her, comes to stand a mere inch away and cups her chin between his fingers, tilting her head up to look at him, “I really don’t mind, okay?”

She nods and Dean smiles, the crinkles around his eyes showing. 

His hands go to the back of her neck, thumb stroking along her jawline. “Did you hurt yourself?”

“Uh-huh,” She says, her tongue still feels rough inside of her mouth and she doesn’t feel like talking. 

Dean grins, “Where?”

She points her index finger to her mouth and Dean grins some more, leans down, presses his soft lips on hers. 

There’s fluttering in her stomach. Why does it flutter? What the fuck is he doing to her?

“Better?” He asks but he doesn’t move away, his lips still ghosts over hers, his coffee breath mingling with her own. 

“Tongue,” She manages to say without opening her mouth too much but she leaves her lips parted a little.

“Show me,” Dean demands, and watches her open her mouth. She sticks out her burned tongue. 

He inspects it at first but then he moves closer, his lips seals around her tongue as he sucks it in. She can’t lie about it. It really does feel good. Dean’s tongue and mouth is smooth against her burned one. 

It feels good but it’s also very bad because now she can’t quite get enough of it and Dean seems to have the same problem because his hands are on her ass and he goes further down, grabs her thighs and lifts her up to sit on the kitchen island. He slots himself between her thighs, kisses her rough and hard, bites down on her bottom lip, making her yelp, and she can hear him chuckle against her mouth. 

“We should go,” She breathes against his lips, feels a little more than out of breath. 

Dean grins, pecks her lips twice more before he takes a step back to look at her, “You look as if you just kissed your boss,”

She swats at his chest, “Seriously, we should get going.”

“Yeah,” Dean agrees, helps her down onto her feet before he takes his jacket and puts it on, “Gabe’s already waiting.”

Y/N frowns at him, “You drive to work?”

He looks at her dumbfounded, “Yeah?”

“Dean, you literally only need to walk two blocks.”

“Wait, does that mean that you wanna walk?”

“Duh,” She grabs her bag and walks to the door, “I mean, you can let Gabe drive you but I’m going to walk. It’s such a beautiful day out.”

Dean’s already on his phone before she can even finish her sentence, “Yeah, Gabe. We’re going to take a walk. I’ll call you when I need you.” He follows her out and locks the door behind him, “Are you happy now?”

She stops in front of the elevator and turns to smile at him, “Yeah.”

  
  
  


*

  
  
  


Dean takes her hand when they step out of his apartment building. She knows it’s for show but it feels real. And it feels good. 

“You know,” Dean tilts his head down to look at her, “I’ve never walked to the office,” He pauses to think, “No, actually, that’s not true. I ran yesterday when I thought that you were leaving. And then I ran back.” 

Yeah, she remembers that. She was so mad at him yesterday and he walked right out of a fucking meeting to stop her from leaving.

“You should do it more often. It’s really a nice stroll. I wish I could live close to the office so I wouldn’t have to be stuck in traffic.”

They start to talk on the way and they walk slower past the coffee shop close to his company. That’s the place she used to work before Dean offered her the job. She wonders if he remembers it too. 

  
  
  
  


*

  
  
  


They arrive on the office floor together with her hand in Dean’s. In fact, he never let go off her the whole way here. Some people are staring and it makes her feel a little uncomfortable. 

When they arrive at her desk, Ruby’s already grinning at her and Dean. Her grin is wide, bright. Y/N frowns at her friend who’s grin just got even brighter.

“So, have a great start,” Dean says and she feels awkward going back to what they were before the whole friends with benefits thing. To what they were before she agreed to be his fake fucking wife. 

“Thanks, do you need me to do something urgent today?” Y/N hears Ruby giggling and turns to her friend, “You, shush!”

She looks back at Dean and sees him holding back his laugh as well. 

“Oh my god, you guys are unbelievable!” She rolls her eyes and Dean pulls her close by her waist, kisses her cheek and her face literally lights up. What is he thinking? Everyone can see!

“I want you to go over my schedule. Cancel whatever I have at lunch. Was thinking we can go get lunch together.”

“Okay,” She nods, and adds, “sir.” 

Dean’s eyes widen and he has to clear his throat upon hearing her address him formally again, “Right. And oh, get me coffee, please? I miss your coffees.”

He turns to Ruby, “No, offense,”

“None taken,” Ruby shrugs it off.

“Sure thing,” She turns around to sit but Dean stops her, his grip tight on her waist. He pulls her against him with force and plants a kiss square on her lips. She turns to putty in his arms and she can hear someone gasping from a distance. She thinks she can hear Ruby whimpering, too. She can’t be sure because, she’s lost in Dean’s kiss again and it drowns out all the other noises around her.

“Good,” Dean whispers when he parts, pecks her wet lips once more before he steps away and lets her sit down. He clears his throat before he walks to his office, “I’ll be in my office.”

When Dean closes the door to his office, Ruby’s on her case right away.

“What the fucking fuck is going on? Oh my god, you gotta tell me! Are you two doing what I think you’re doing?” There’s a smirk on her friends face and she even wriggles with her eyebrows.

“Shhhh!” She hisses at Ruby because she’s so fucking loud, “I’m his wife remember? Of course we do—” She gestures widely with her hands, “—things!”

Ruby snorts out a laugh, “That’s why he was in such a good mood yesterday! Although he nearly fired me.”

Y/N starts her computer and types in her password, “Yeah, what was that all about? He told me that he almost fired you.”

“It was really a stupid thing. He apologized, though. So it’s okay.”

“Aaaand you don’t wanna tell me why because…” She raises her eyebrow at Ruby.

“Your brother called and Mr. Winchester got mad because I didn’t interrupt him and put Jack straight through to him.”

“What?!” Y/N’s mouth stands agape.

“Yeah,” Ruby sighs, “Like we both know how he is when he gets interrupted when he’s in a meeting.”

That’s true. Ruby’s not wrong. Dean absolutely hates when someone interrupts him when he’s in a meeting because that would divert his attention and it’s hard for him to clear his head again to focus on the matter at hand. That’s why she was also baffled that he left a meeting just to make sure that she won’t leave. 

“So, tell me,” Ruby grins up from her screen, “Does he have a stick up his ass?”

  
  
  


*

  
  
  


The first day back at work was okay. She has spent her breaks with Ruby and filled her in on everything Ruby wanted to know. Maybe not really everything though, because there are things she likes to keep to herself. Like that they already had sex and that Dean ate her out, and that they decided to be friends with benefits. 

Dean took her out for lunch and they went to grab a burger around the corner. The people warmed up to the idea that she’s his wife too. At least she hasn’t heard anyone saying bad things about her, not even behind her back, and if they do, she is sure that once Ruby got wind of it, Ruby will give them an earful. 

Y/N’s on her way home after a long and stressful day. Turns out that she was more needed than she first thought she would be. She’s walking home alone this time, because Dean went straight to a meeting he has with Sam about the marriage thing before Sam would meet with Amara, and she’s not needed. Even though Dean asked if she wanted to join, she really didn’t want to intrude.

Instead, she’s going to go out with Ruby tonight. Apparently, Ruby’s favorite bar is holding a karaoke night. 

Come with me, Ruby said. It’d be fun, Ruby said. And that’s why she’s on her way to change and then she’ll meet Ruby. She’s still allowed to do that, right? She’s allowed to go out and enjoy herself. Sam just said that she isn’t allowed to flirt or date or have sex. Things which she’s doing but basically with her fake husband who’s also her boss.

How did her life get so complicated?

  
  


*

  
  
  


Y/N turns up at the bar and she sees Ruby sitting at one of the little tables. Right in front of her is a mic stand and there’s a big monitor. Someone’s already singing too, some strange interpretation of  _ Staying Alive _ .

Ruby waves at her when she sees her. 

“Oh my god, Ruby, seriously? Karaoke?” Y/N wrinkles her nose at her friend and Ruby just shrugs and takes a sip of her drink. 

“Drink some, it’ll be funnier if you do!” Ruby shouts out above the music.

It seems to be a good idea, so Y/N orders herself a gin. 

After about her third gin, she can see that Ruby’s right. It really is much more fun if you’re tipsy. She’s still not drunk enough to go and sing herself, though. But she bets that she can talk Ruby into singing. 

The people who go up to sing are either drunk or — no, they are definitely  _ all _ drunk. Some more than others. It’s funny, really. She likes the atmosphere and she thinks that it’s probably not going to be the last time that she’s going to come here. 

Her phone lights up when someone finishes their own version of  _ I Will Always Love You _ , and she takes a look at her screen to see that it’s Dean.

He had called her too, apparently, because she has two missed calls from him. She was so lost in having a good time that she didn’t even feel her phone vibrating and it’s just pure luck that she sees it now.

_ D: What are you up to? _

_ Y/N: I’m at a bar with Ruby. You? _

_ D: Meeting just finished. What bar? _

_ Y/N: 7th street. O’Malleys. They are having a karaoke night. _

_ D: Oh no, you need to be drunk for these kinds of things. Are you drunk? _

_ Y/N: Not yet. _

_ D: Good, I'll be coming with Sam. _

_ Y/N: You really wanna come and listen to other people singing? _

_ D: Hey, a bar is a bar _

She laughs to herself and sees Ruby raising an eyebrow at her, “Dean said he’ll be coming too and he brings Sam.”

“Oh my god, Sam is coming? Shit,” Ruby threads her fingers through her hair, tucks strands behind her ear and rights her cleavage, “How do I look?”

“You look absolutely stunning,” Y/N says, she’s already feeling light headed, “All the women want to be like you and all the men want to be with you.” There’s a cheeky grin on her face as she eyes Ruby who’s frowning a little.

“Ha-ha, shut up.” Ruby hisses grumpily, “I really like Sam. You think he’s still single? Is he looking for something? I don’t even mind a one night stand, I just wanna feel his cock inside of me.”

“Oh my god, Ruby!”

The other woman shrugs, “What? I know what I want, okay? I’m not ashamed of it.” 

“You’re drunk.” Y/N says teasingly.

Ruby raises her eyebrow, “Oh come on, don’t tell me you haven’t been thinking the same about the bossman. Who, by the way, I would also like to spend a night with but he’s off limits now.”

Yeah, because he’s married to her, she thinks. But even if he’s not she would probably be more than jealous if Ruby had something going on with Dean.

Y/N takes her friend’s hand, and looks her in the eye, “Ruby baby, honestly? You look great and if Sam’s single, he would be an idiot not to want you.”

“You think so?”

She nods at Ruby, “I think so. You’re so fucking pretty, sometimes it makes me jealous that you get all the attention.”

“Now you’re just crawling up my ass.” Ruby snorts. 

“Hey, it’s warm and cozy in here.”

  
  
  



	9. CH09

Sam and Dean show up about thirty minutes later, right when she finishes her fourth gin. 

They make a beeline to where she and Ruby are sitting, grab themselves some chairs that were standing around unoccupied and sit themselves next to them. Someone is singing  _ Bohemian Rhapsody _ and people are cheering along.

“Hey,” Dean greets them both, looks from Ruby back to her, before he shrugs off his jacket and drapes it over his chair. He folds his shirt up to below his elbows and Sam follows suit. 

God, they really look so good, both of them. They really put all the other men in here to shame. And the women are talking behind their backs.

“Hey, how was the meeting?” She asks, and sees Dean rolling his eyes, it’s the answer to her questions, she knows. And she frowns because she’s a little scared that they might lose after all. 

Dean notices the change in her face, leans in to place a kiss on her cheek before he rests his head on her shoulder. He mumbles to her, “We got this, don’t worry.”

“More drinks?” Sam asks into their round, and beckons the waitress over. 

Both she and Ruby nod their heads.

“You want more?” Dean asks her with one raised eyebrow, “Or will you be too drunk?”

“Hey, I’m not drunk.” She says but she thinks that he can see it in her cheeks that she’s very tipsy. Maybe she’s already drunk, she doesn’t know. The line’s very slippery between tipsy and drunk. One misstep and she’ll be on the other side.

“Liar,” Dean shrugs with a grin, “I’ll allow one more. I need you sharp tonight.”

Before she could even ask what he meant by that, he had ordered her a drink and they began to talk about other things. 

It’s when Sam suddenly stands up to walk to the front that they all started to cheer for him. 

Sam walks to the DJ and whispers something to him before he walks back and grabs the mic. He clears his throat, and she can’t help but laugh.

“Oh no,” Dean groans, feeling second hand embarrassment, and he shows the waitress a sign before ordering two more drinks for himself. “Gotta get on your level to enjoy this,” He whispers to her.

The music starts and everyone starts cheering. 

And then they’re waiting for Sam to start singing, “I believe in miracles,” Sam sways his hips, “Where you from, you sexy thing,” He winks at Ruby and she can swear that her friend whimpers and squirms in her seat.

“I believe in miracles, since you came along, you sexy thing,”

Y/N’s full on laughing and Ruby blushes. 

Sam takes off his tie and swings it around.

“Oh, man,” Dean rubs at his face and she has to laugh at him.

While Sam’s singing, Dean places his hand on her thigh, strokes it up and down and leans closer, rubs his nose along her cheek, “How are you feeling?”

She tilts her head to him and he catches her lips, kisses her soft and tender. His hand cups her face. 

He grins when he parts, strokes the pad of his thumb along her cheek and she smiles, too. “Light headed, but good,” She answers him.

Dean looks at her, presses his lips into a playful grin, “Not too drunk for what I’m going to tell you, I hope.”

“I’m listening,” Her heart thumbs in her chest, curious but also a little scared of what he has to tell her.

He leans closer to whisper into her ears, “I’m taking you on a honeymoon.”

“Dean, no,”

“Dean, yes,” He chuckles.

“But the court thing?” She raises her eyebrows, frowns a little too.

“It was Sam’s idea,” Dean jerks his head to the front where Sam finishes his song and they paused their conversation to clap and cheer for him.

When Sam walks back, he sits down with one hand draped on Ruby’s chair and she’s basically all over him, looking at the younger Winchester with heart eyes.

“So,” Dean drapes his arm over her chair as well and one hand is still on her thigh, “What do you say? We leave on Saturday. Ten full days.”

“Dean, you really don’t have to.”

He lets out a huff of air, “It’s good if we go. Someone will notice us, they’ll see us on our honeymoon,”

“Someone will notice  _ you _ , you mean.”

Because that’s the way it is. People recognize him sometimes, and they don’t really care about her. But Dean might be right. If someone sees them it’s even better for their case.

“You’ll be recognized, too. So I have to make sure that it’s going to be alright for you.”

She bites on her bottom lip, thinks long and hard. 

Suddenly Ruby’s laughing and she watches her friend get up to walk to the mic.

“Oh, no,” She clasps her hand over her mouth and Dean laughs while Sam claps his hand and lets out a loud whistle.

The music starts playing and Ruby turns her freak on when she sings, it’s when she gets to the chorus where it gets wild, “I wanna kiss you all over,” Ruby points her finger at Sam, winks at him, “And over again,”

“Oh my god,” She groans but Sam’s smiling from ear to ear.

Y/N turns her head to see if Dean’s laughing at Ruby too, and she finds him grinning. Instead of watching Ruby, though, Dean has been watching her. He lifts his one eyebrow as if he—

—oh, yes, he’s waiting for an answer.

“Uh, I don’t know, on Saturday? But work..”

“Don’t worry about that. I’ll cancel everything and the ones I can’t cancel, I can do them in Jamaica.”

“Ja-what?!”

Dean chuckles, “You heard me,”

“No,”

“Yes,” He smiles, and her hand goes up to cup his face, she can feel the scruff pricking the palm of her hand, “You have a passport, right? Ruby told me you have one.”

“Yeah,” She nods. She does have one because she wanted one, not because she was going to go traveling. 

It’s her that kisses him now, and she teases her tongue along his teeth. Their tongues meet, it’s nothing like the kisses they shared before. It’s teasing, playful. It leaves her wanting more. And then she remembers. He wants to fucking take her to Jamaica!

“Okay,” She grins, pecks his lips, “Do you want me to book tomorrow?”

Ruby sings something off-key and they both have to look her way. 

Dean’s chuckling next to her ear, “Nah, I already sent Ruby the details this evening. You think she’ll be able to come to work tomorrow? Jesus, I can see her panties when she lifts her leg like that,” He turns his head to bury his face into the crook of her neck and she’s laughing, her hands go up to stroke the short hair on the back of his head.

“She’s a professional at work, you know that.” Y/N reassures him.

He looks up right when Ruby is finished and they clap for her. Sam even gets up from his chair, giving her a standing ovation. 

“Well, if Sam will let her go to work at all tomorrow,” Dean scoffs in the direction of his brother.

When the clapping and cheers die down, Dean whispers to her that they should go home and she agrees because it’s late. Dean gets up from his chair and immediately Sam shouts to the front that Dean’s the next singer.

Dean stands there, frozen, “What?!” He hisses at Sam and Sam just laughs and shrugs his shoulders.

Ruby joins in, calling out Dean’s name and Y/N can’t help to cheer with them. Dean sends her a glare and she immediately shuts up and tries to hold in her laugh.

“Come on, Dean!” Sam shouts out, clapping way too loud.

“Please?” Y/N looks up at Dean who’s still standing there, his hands in his pockets. 

“Y’all owe me,” He grumbles as he walks to the front and she wonders what song he’ll pick.

He walks to the DJ and after Dean whispers something to him, Dean turns around and looks into the audience. His eyes quickly find hers.

When the music starts, Dean grins and there are people cheering him on.

_ Oh, no. _

_ Kokomo. _

Dean looks at her when he sings, “Aruba, Jamaica, oh I want to take ya, Bermuda, Bahama, come on pretty mama, Key Largo, Montego, baby why don't we go, Jamaica..”

Y/N starts to laugh and buries her face into her hands. 

When she looks up again, Dean’s still grinning while he sings. 

“Afternoon delight, cocktails and moonlit nights. That dreamy look in your eye, give me a tropical contact high..”

Dean finishes his song and to her surprise, he got the most cheers, and that of course, makes him so fucking proud because he’s smiling at everyone with that boyish smile of his.

“Now Y/N!” Sam says, and she looks over to send him a glare but instead of the glare, her eyes widen because Ruby sits on Sam’s fucking lap.

“Nah, I’m good.” She shakes her head. 

Dean walks over to weave his arm around her waist and kisses her temple, “Okay, let’s go,” He picks up his jacket and they are already turning around when Dean stops to turn back to Sam, “Good luck tomorrow, Sammy.”

Sam just lifts his hand to a salute.

Dean’s still humming when they sit in the Uber and she has to chuckle.

“You seriously still humming The Beach Boys?”

Dean groans, “Can’t help it. I have it in my head now.”

  
  
  


*

  
  


The ride in the Uber was kind of bumpy and when they arrived, she felt somewhat dizzy. In hindsight, maybe she shouldn’t have taken that last drink. 

Of course Dean has to notice and is quick by her side, “You okay?” 

She nods, “Yeah, just— maybe I had too much to drink.”

“Come on, let's get you inside,” He has one hand firm around her waist and helps her to the elevator.

Inside, Dean lifts her up to sit on the kitchen island and goes to grab a bottle of water from the fridge. He opens it and holds it out for her to take before he walks to his room wordlessly.

She wonders where he’s going but then she hears him walking back. He grabs her wrist and places two Tylenols into the palm of her hand.

“Take it and drink up,” There a frown etched deep in his face and he watches her as she downs the pills and drinks up the water. 

He picks her up after she drinks, carries her to her room she assumes, but then he opens up the door to his own bedroom.

“Dean, I need to clean my face and brush my teeth,”

“Right,” He mutters and backs out of his room to go into hers. He walks straight through to the bathroom but instead of setting her down, he lowers himself with her still in his arms, “Take the things you need,”

She doesn’t really know why she needs to take her things, but she does and has to laugh when her hand misses picking up the toothbrush twice.

“You got everything?”

“Uh-huh,” 

Dean walks her out and right into his room again.  _ Oh my god _ , does he really want her to sleep in his room tonight?

He sets her down in his bathroom and tells her to get herself ready for bed before he walks out.

Y/N doesn’t feel like arguing, so she does what she’s told, and starts to clean her face. 

When she’s brushing her teeth, Dean walks in and sets something on the sink. She can’t really see because he’s now behind her and he is only in his underwear. Distracting is what it is.

Dean doesn’t push her aside but instead, he works around her, crowds her in as he reaches for his own toothbrush and begins to brush his teeth. She can see him watching her through the mirror.

She finishes and rinses her brush and Dean hurries to finish as well. He turns her around, cups her chin and makes her look up at him, “You feeling better?”

“Yeah,” She breathes out, because it’s true. After drinking so much water she feels much better already.

“Good,” He nods and then he begins to take off her dress. She didn’t wear a bra so as soon as Dean slips the dress over her head, she covers her boobs and Dean has to laugh at that, “Y/N, it’s really nothing I haven't seen before.”

Yeah, he might be right but still?

He takes the shirt he placed on the sink and pulls it over her head, lets her slip into the arms of the shirt.

“Let’s go to bed,” Dean’s already pushing her towards the door but she stops him. “What?” He asks with a frown.

She has to giggle at the worried look on his face, “I just drank so much. Where do you think it all goes?”

“Right,” He mutters, blushing a little too. She thinks it’s cute. Dean pats her shoulder before he walks out and she closes the door.

When she finishes and switches off the light, she needs to wait a couple of minutes for her eyes to adjust to the darkness. 

It doesn’t take long, only a couple of blinks to see Dean’s face bathed in moonlight. He looks good, like a perfect oil painting, the cover dragged half across his body. 

Dean lifts the covers, pats the space next to him, and she goes in willingly. How can she not?

He holds out his arm for her to lay her head on and she likes that, it makes her feel safe. She snuggles up to him, even after a tiresome day he still smells so good. It’s making her even more light headed. 

“Why am I sleeping here?” She has to ask for her own peace of mind.

Dean kisses the top of her head, “Because I wanna know that you’ll be okay in the night.”

After a while of silence, Dean starts to hum  _ Kokomo _ and she lifts her head to glare at him, “Really, Dean?”

“I can’t help it,” He chuckles and turns to his side, drapes an arm around her waist. He noses at her temple and sings into her ear, “Aruba, Jamaica, oh I want to take ya,”

“Oh my god,” 

“Bermuda, Bahama, come on pretty mama,”

“Are you really sure you can take the days off?” She tilts her head up, her nose meets his scruff.

“Super sure,” He leans back a little to look her in the eyes, “When was the last time you remember me taking days off?”

She pauses to think and yeah, he’s right, “Never?”

“Exactly, and if I remember correctly, you have only taken a couple of days yourself. Five, was it?”

How does he know? He must have looked into her records. 

“Yeah,” She says, “Mostly when Jack’s home from college.”

“So, we’ll go away, get tanned, drink cocktails and you always wanted to go there, haven’t you?”

It blows her mind that Dean remembers that conversation. It’s only yesterday that they spoke about it but still, she never thought he would put so much weight into her words. 

“Yeah,” She smiles.

“Good,” Dean grins and leans down to kiss her. It’s really tender and he’s playful with his tongue, teases her own tongue enough to make her whimper. He’s such a good kisser and she absolutely hates how addicted she is to him, “‘K let’s sleep. We have work tomorrow.” Dean pecks her lips once more and she lets out a frustrated groan which, in turn, makes him chuckle. 

With a last good night kiss, she turns around on her side and it’s not long until Dean finds his way to her, and spoons her from behind, his arm draped protectively around her. She can feel the bulge in his pants. He’s half hard, at least. Y/N can’t help but press her ass against his groin and she hears him hitching his breath.

“You should stop that.” One of his hands tight on her hip now, to keep her from moving.

“Why?” She sounds whiny but she doesn’t care. She blames it on the alcohol.

“Baby, because you’re still half drunk and I’m not doing you like this. Stop trying, you can’t change my mind.”

Wow, Dean definitely has more self control than she does.

“Fine,” She pouts.

“You know,” He says, blanketing her with his body as he makes himself comfortable, “I can’t remember if I’ve said it before, but I’m happy that it’s you.”

She can hear his even breathing behind her, and is thankful that he can’t see the blush in her face.


	10. CH10

A very loud, very piercing sound catapults her wide awake and Y/N almost stands up straight in bed upon hearing the unfamiliar noise.

There’s a shuffling sound of a hand taping on a night stand. It needs too many misses to finally stop that horrible, horrible noise. When silence returns, she closes her eyes again.

It takes her a little while to remember where she is and when she does, her eyes fly back open with horror.

Blinking, she sees that she’s still in Dean’s room, still horizontal in his bed and she feels him, feels his legs, his arms, his body. They’re connected and tangled together in more places than they’re not.

She knows that she should maybe get up, should maybe hop into the showers and get dressed for work but she just can’t seem to move because he’s half draped over her, and strangely, she’s very okay with that. It’s too cozy in bed to want to move at all. So she does what every sane person would do after the ringing of an alarm — she closes her eyes again.

Another shrill noise snaps her out of her cozy cocoon after a while.

_ Oh my god,  _ that fucking alarm again!

Dean stirs next to her, his hand flies to where his alarm is, picks it up and throws it against the wall, the ringing dies down. He slips his hand underneath the covers, arm weaving around her waist. 

“No wonder you’re always so grumpy,” She mumbles into the pillow, catches his scent off of it.

Y/N feels Dean lifting his head to look at her.

“What?” His voice is deep and raspy, still full of sleep, the bass of it vibrates onto her back.

“Your alarm. It literally makes me angry hearing it.”

He chuckles at that, “I have to buy a new one now anyway.”

She turns onto her back and tries to blink the sleep out of her eyes and then she looks into Dean’s eyes who is propped onto his elbow looking down at her.

_ Oh my god _ , how can he look so good so early in the morning? It’s not fucking fair! His hair is ruffled up but it makes him even more cute.

“What time is it?” She squints her eyes, looking at him feels like looking into the fucking sun. Her eyes can’t take it so early in the morning.

“6.15am,”

“What? Oh my god, Dean!”

He chuckles as she buries her face back deep into the pillow, she takes another breath of his intoxicating scent.

Dean kisses her temple, “Come on! Rise and shine, Y/N!” 

“No,” She mumbles.

His hands find her under the covers to tickle her and she’s squirming in his grip, “Oh my god, okay, okay! I’m up!”

Dean gets out of bed to walk to the bathroom and she follows grumpily. She avoids looking in the mirror because she would then see what she knows. That she looks like she’s been run over by trucks — repeatedly. 

He’s already brushing his teeth and she picks up her toothbrush while he helps her squirt toothpaste on it. With a glare, she places the brush into her mouth and walks out of the bathroom.

“Where are you going?” Dean calls after her.

“I’m taking a shower.” She answers, and proceeds to walk into her own room. 

There, she gets out the shirt, tosses it on her bed that’s still made since yesterday morning. Getting out of her panties, she balls them up and throws them into the hamper. She continues to brush her teeth as she walks to the bathroom and sits down to pee. After flushing, she spits out the toothpaste and rinses out her brush before she gets into the shower. 

She’s in the middle of soaping up when Dean walks in naked like a fucking greek god. He clearly has no shame whatsoever. But again, she probably would have none either if she looked like that.

Dean leans against the sink, she can’t really see him in detail because the shower glass begins to fog up. She can see his outline, can see that he crosses his arms over his chest and there’s a chuckle, “You’re not a morning person, are you?”

“Ya think?” She grimaces and rinses the shampoo out of her hair.

He ignores her snarky remark and steps into the shower. From up close she can see that his body’s still damp, little droplets of water resting on his shoulders. He already took a shower. And then her eyes wander down to his boner. Yep, definitely hard and it definitely looks inviting. It makes her knees weak and he grins cockily because he knows. Damn him.

She rinses the foam from her face and when she opens her eyes again, Dean’s right up in her space as he cradles her head between his big palms and tilts her face up to look him in the eye.

“How are you feeling?”

“Good,” She replies, “Just angry about your alarm clock,” She’s pouting a litte.

Dean chuckles, “You can order me a new one. See it as one of your tasks for the day. Order something that has a less penetrating sound.”

“Oh, I will. Maybe then you’ll be less grumpy in the mornings,”

“Hey, I’m not the grumpy one around here right now.” He grins and leans down to kiss her. 

It’s soft at first, he’s gentle, as if he’s testing the water. It only grows heavier when she kisses him back. She sucks on his tongue like he normally does to her and Dean groans against her mouth. 

“Fuck,” He breathes out, “What are you doing to me?”

What is she doing to him? More like what is he fucking doing to  _ her _ ?

He picks her up, and the next thing she knows he has her pinned against the tiled wall. The impact makes her bite down on his bottom lip that’s still attached to her, and he groans some more at that. 

It’s all rough and need and want, and her mind is fogged as much as the shower, her pussy clenches and releases around nothing.

Dean nibbles down her throat, “You want this? Tell me you want this,”

How is she supposed to answer him when he sucks down her throat and thrusts his hips so his dick grinds so good against her aching cunt?

She tries nonetheless, “Y— oh go—, ye— ss,” 

There goes her coherent thoughts.

He kisses around her lips, plants little pecks on her nose, her cheeks, “Next time, I promise, I’ll take my time,” His breathing is ragged, “I just— fuck— just want to feel you around my cock now, can I?”

“Please,” She stammers, doesn’t even care that it came out whiny.

He smiles, kisses her and lines himself up with one hand while the other one still holds her pinned against the shower wall. 

Dean takes his time now, threads the head of his cock along her folds, slicks it up with her juice before she feels him at her entrance. He goes in slow, and she feels the stretch and burn and he moans into her mouth upon feeling the warmth of her pussy.

“Goddamn it,” He lowers his face to the crook of her neck, sucks at her skin and her hand fists in his hair, one is on his back, nails digging into his flesh.

“Dean,” She whines out, because he’s still moving awfully slow. He pauses and his body shudders when he bottoms out.

His thrusts stay slow, as if he doesn’t dare to hurt her.

“Harder, please,” She needs it. Fucking wants him to have his way with her.

He chuckles, his mouth leaves her skin, and there’s skin between his teeth that he releases before he kisses it to sooth it, “Harder, yeah?”

“Uh-huh,” 

“Christ,” Dean curses, picking up speed and she wedges an arm between them to rub at herself, “Dammit, you’re already tight as it is but you rubbing yourself? It just got wetter and tighter. Keep doing it, baby,”

_ Baby. _

Okay, she really loves it when he calls her that, not going to lie. The endearment goes straight to her core and Dean curses some more as her pussy pulses around him. She can feel it too.

“You’re killing me,” He kisses her deep and with the same roughness he fucks up into her.

She wants to tell him that he’s the one who’s killing her— but she can’t, because her toes are curling and there’s a growing sensation in the depths of her core. It gets stronger and stronger. 

“Fuck, yes, yes, yes, don’t stop don’t—”

The explosion hits her whole body, she’s shaking above him and Dean has to hold her tighter so as not to let her slip out of his grip. Her hands fly around him, scrambles at his back for purchase. She’s sure that she’ll leave a mark on him, hoping that he doesn’t mind. He groans too, his voice deep and loud as he buries his face deep into her neck and he shudders all over. 

When he comes down from his high, he chuckles, kisses up her shoulder, her neck, her cheek until he meets her lips, “You’re fucking amazing, you know that?”

She blushes at that, but fortunately her cheeks are already flared up from the fucking, “You too,” She smiles and Dean kisses her again before he sets her down. She squirms at the loss when he pulls his still half hard cock out of her with another peck on her nose. 

Her legs are wobbly and Dean helps her standing up straight while he places her back under the spray and begins to soap her up. He groans out when his hand goes down there and his fingers slips along her folds. It’s still slick and full of his cum.

Y/N does the same to him, squeezes body wash into her palms and begins to soap up Dean’s chest. She can feel every bump, every muscle twitching, he’s so firm but soft at the same time, it’s ridiculously sexy, and she can’t believe that she’s married to him! Well, fake married— potatoes, potatoes...

Her hands go further down, and she feels his stomach clench when she’s soaping him up underneath his navel. Dean groans out when she grabs his dick, working both hands around his length that’s already increased in size.

Dean groans out, his lips capturing hers for a kiss before he parts, pulling his lower body away from her. His mouth ghosts over hers, their minty breath mixes with the scent of her body wash, “Baby, you gotta stop that or else I have to fuck you again.”

She raises her eyebrows with a cocky grin because she really doesn’t know if it’s a threat or a promise.

Dean rolls his eyes playfully, groans out a little, and he makes her let go of his cock causing her to pout, “Jesus,” He surges forward, teeth sinking down onto her bottom lip as she yelps up with a giggle.

Of course he’s right. They don’t have that kind of time, so she rinses herself out and Dean follows her under the spray. The smell of her body wash fills the room, the scent hangs heavy and humid in the air and she has to grin at him.

“What?” He asks her with one eyebrow raised as she walks over to her towel and starts to dry herself off. 

She starts to chuckle, “You’ll smell like my body wash now.”

Dean just shrugs like he really doesn’t care and continues to wash away the foam from his body.

  
  
  


*

  
  
  


She has to hurry, she knows, because Dean’s already finished and he told her that he’s waiting for her, but she really doesn’t know what she should wear today. 

In all honesty, she doesn’t  _ really _ have many choices but her head’s still hurting and it seems like she has a hard time getting her makeup right. 

She opts for a dress. It seems like the best choice because there aren’t any buttons she has to deal with and as for the makeup? Powder and mascara it is. And instead of lipstick, she just uses gloss. She really doesn’t want to waste energy on how she dresses when she knows that the day ahead will be stressful as it is. Sure, it’s Friday, but they always have a lot to do on every freaking day of the week. And— oh shit! She’s going away tomorrow, so she will have even more to do and to arrange for her and Dean’s absent.

“‘M sorry, I’m making you late again.” She groans when she walks into the living space and comes to stand next to him and Dean hands her a cup of coffee. She stares at it.

“Don’t worry, it’s already cooled down a little,” 

She has to grin at that, “Thanks,”

“Take your time,” Dean says and turns a page of the newspaper that’s spread in front of him.

She takes a seat on the stool at the kitchen island and lays her cheek on the cold surface, still feeling so hungover, “I think we have to go, my boss will kill me if I’m late,”

Dean chuckles but doesn’t look up from the paper, “I think we’ve established that your boss is a dick.”

“Yeah, and now,” She drinks half her coffee, “I’m definitely going to be late,”

He looks up from the papers, “You want breakfast? I think I still have toast somewhere,” 

“Dean, are you listening to what I’m saying? We’re late! My boss will definitely call me into his office. And no, ugh, I don’t think I can keep solid food down,”

Dean raises an eyebrow. He’s already in his suit jacket, the tie neat and he even wears cufflinks. He presses his lips together into a smile as he watches her down her coffee, his dimples of content are showing. A rare sight.

He abandons the newspaper and comes to stand behind her. His arms on either side of her body as he braces his hands on the surface of the kitchen island crowding her in. She feels him lowering himself behind her to whisper into her ear. She feels hot all of a sudden, “I think he’ll be okay with it,” He noses behind her ear, making all the hair on her back stand up, “And if he calls you into his office, it’s not because you’re late.”

  
  
  
  


*

  
  
  


They arrive and Ruby’s already there, although not really, because she’s slumped over her desk.

Dean squeezes at Y/N’s hand that’s still in his and they stand next to Ruby’s desk, which is the opposite of Y/N’s own desk. He tries to keep a straight face as he clears his throat loudly next to Ruby.

“Huh? Shit! Yeah, I’m here,” Ruby sits upright, is startled by the noise and she looks up at the source to see Dean and Y/N grinning. Her friend’s face falls, “Sorry, sir— I’m—”

“Ruby,” Dean says, and he let go of Y/N’s hand to let her sit down at her desk, “If you could work? That’d be great. And if you need to sleep, go take a nap in the break room like everyone else does.”

Y/N’s jaw drops. How does he know? He’s never in there! 

“I need to see you,” He tells her, “You got my email, right?”

“Yes, sir,” Ruby scrambles to gather the papers together and stands up.

“Is my brother in?” He asks. Sam’s office is situated a floor below them. 

“Yes, sir.”

Dean raises his eyebrow, “You had a good night?”

Y/N tries to hide her grin.

“Yes, sir.” Ruby’s cheeks turn red.

“You can go wait in my office, I’ll be right there,” Dean says and Ruby nods, walks towards his office.

Dean smiles at Y/N and then he takes a step closer, cages her in with one hand on the back of her chair and one braced on the desk. He lowers himself enough to whisper into her ear, “Did you notice too that Ruby’s still wearing the clothes from last night?”

She snorts out a laugh, “Yeah,”

He laughs with her, places a kiss on the top of her hair, “Okay, let’s work, shall we?” Dean turns around and walks to his office.

“Dean?”

Y/N watches him turn around, “Please don’t tease her about it?”

He shrugs, leaves his hands in the air, “Of course, I won’t. What my employees do in their own time is none of my business.”

“What am I  _ doing _ as well?” She raises an eyebrow.

He replicates the rise of the eyebrow, his hands disappear into his pants pockets and he grins cockily, “You’re doing me, so yeah, that is my business. Now order that damn alarm clock or I’ll need to see you in my office next.”


	11. CH11

Y/N watches as Ruby comes back out of Dean’s office. Ruby’s smiling but her smile doesn’t quite reach her eyes. She knows that Dean wants to see Ruby first thing because he wants to make sure that she is following his instructions on booking a trip for them. And suddenly, she feels guilty because Ruby knows that they’re going on their fake honeymoon, and she kind of hopes that Ruby’s going to be okay with it. 

“Oh my god,” Ruby groans, and lets herself fall into her chair, “I’m so fucking hungover.”

“Ugh, tell me about it,” Y/N agrees with her friend.

Ruby begins to work in silence and Y/N frowns. After a while she looks up from her computer screen and speaks up, “So, you wanna tell me about last night or?”

Her friend lets out a sigh, “Oh my fucking god, I’m so glad you asked!”

Y/N giggles. Ruby’s always so fucking dramatic, she loves it.

“So, did you go home with who I think you went home with?”

“My god, Y/N, it was magical! Magical, I tell you!” Ruby gushes, “But let me book that trip for you first and then we’ll go grab a coffee.”

“You okay with me going on a honeymoon?”

“Duh, I’m so happy for you! While you’re there, you can make him fall in love with you for real!”

“Ruby!”

“What?” Her friend gasps, “Just saying. I mean, have you seen how he treats you, how he looks at you? The woman who gets to marry him for real is one lucky bitch! I wish that was you because in all honesty, you deserve everything good, alright?”

“Yeah,” She says and doesn’t know what else to add to it, but looking at Ruby, she doesn’t have to because Ruby’s already on the phone with the travel agency.

  
  
  


*

  
  


Turns out that they didn’t have time for that coffee but they did go grab lunch at the coffee place close by and sit down on a bench right in front of their office building to have a little chat.

Y/N looks at her sandwich suspiciously. She’s still not sure if it’ll stay down. She takes a bite nonetheless, because she knows that she needs something in her stomach if she wants to survive the rest of the day. 

“So, Sam,” Y/N says while she chews. She looks over to Ruby, sees her friend tense up and she sees the blush in Ruby’s face. The woman rarely blushes so it’s even cuter to see it.

“Yeah, Sam,” Ruby tucks her brown hair behind her ear and bites down on her bottom lip as not to whimper out at the details of what happened last night.

“So,” Y/N raises her eyebrow in question.

“So,” Ruby gushes.

Y/N rolls her eyes and groans out in frustration, “Ruby! My god, just tell me, I’m dying here!” 

Her friend starts to giggle and the redness spreads to her cleavage. 

“Did you?” She asks, hopes that Ruby will finally tell her what went down (or rather who went down) last night.

Ruby’s chewing on her bite of sandwich and speaks with her mouth full, “We wanted to, but we didn’t, no,”

“What?” The bite Y/N took almost falls out of her mouth.

“I’m telling you, he’s a real gentleman, Y/N! Said he didn’t want to take advantage of me being drunk,” Ruby takes another bite, her lips curl up around the sandwich, “But I felt it.”

“You felt it?” She frowns.

“We slept in the same bed. And he was hard because we made out.” Ruby’s grinning at the image on her mind, “God, he’s such a good kisser. Just the way I like it. Rough but tender, and he’s big.”

Okay, so they’ve established that both Winchesters are gentlemen and they are both good kissers. Great. Life’s not fucking fair that two brothers have it all and they can easily put every other men to shame. 

Y/N frowns some more, but in a playful way, “Big?”

Ruby sighs, “Yeah, big hands, big feet, big—” She wriggles with her eyebrows, “—You know what!”

“Ooookay,” Y/N snorts out, “That’s too much information, but thanks for letting me know,”

“We’re going on a date tonight.” Ruby says nonchalantly, as if it’s no fucking big deal.

“You what?” 

“Yeah,” Her friend smiles, “And I’m not drinking if you know what I mean,” Ruby wriggles with her eyebrows again. She should stop doing that because Y/N knows exactly what she means without that stupid eyebrow wriggling.

Y/N’s truly happy for Ruby and she’s super happy that Sam treats her right.

When they finish their lunch, they notice a limousine coming to a halt right in front of the building and Amara steps out.

_ Oh, no. _

That’s right, Sam has a meeting with her today. She almost forgot.

“Ugh, I don’t like her at all,” She says and Ruby wrinkles her nose at Amara too.

They walk into the building right ahead of the woman, hoping to get away on time but Amara’s close on their heels and the woman already starts to drop a remark, “Nice dress, where do you get it? Thrift store? Your husband didn’t even give you enough money to buy something decent?”

Y/N bites on her tongue so not to bite back at that stupid bitch. She really doesn’t feel like confrontation, and especially not one with people who she couldn’t care less about. It’s just not worth her time or energy, nor is it worth her patience that’s running thin today. So they just walk ahead to the elevator while Amara has to report to the front desk. Crisis averted.

After her lunch, Y/N sits down to do more work when she sees Dean walking out of the meeting room. He stops at her desk and asks her to bring him coffee. He had a meeting about investing in another company on the west coast, but she thinks that it might have not gone well because he looks a little downcast. 

“You okay?” She asks, and Dean snaps out of his trance. 

“Huh,” He sighs, “Yeah.”

“You had anything to eat yet?” She looks at him, concerned.

“Yeah,” He breathes out, “Garth ordered pizza for the meeting.”

“Okay,” Y/N says and smiles as an attempt to cheer him up, “One coffee coming right up.”

Dean smirks at her, “Thanks, I’ll be in my office. What’s my schedule?” 

“Well, you’re free for another hour.”

“Good, I need a break.”

He turns on his heels to walk into his office.

Ruby’s staring at her, “Wow, he’s not in a good mood, isn’t he?” 

“Doesn’t seem like it.” She agrees. 

“But he didn’t lash out, so at least there’s that.” Her friend shrugs, as she starts to type in an email.

“Yeah,” Y/N sighs, “At least there’s that.”

She doesn’t really know what it is but seeing Dean like that does not make her feel good at all. She likes the happy Dean, the playful Dean. Not a Dean who thinks he lost a goddamn war.

Walking along the hallway with Dean’s coffee in hand, she knocks at his office door first before she goes in. 

He’s sitting at his desk, looking over a contract that she has placed there while he was in the meeting. He doesn’t seem to notice her.

Closing the door behind her, she walks over to him and sets the coffee on the desk, “Your coffee,”

“Huh,” Dean looks up from the papers, “Yeah, thank you.”

“Is there anything else I can do for you?” She asks but Dean’s lost in his work so she turns to leave. Doesn’t feel like disturbing him more than she has to. 

“Wait,” He suddenly says, “Come back,” 

She stops mid room and turns around to see him smiling. 

“Sorry, I had to finish reading that paragraph,” He explains and she smiles back at him, walks back to stand beside him. 

Dean moves his chair back, takes her wrist to pull her into his lap, making her yelp up and he chuckles at that. His arms are quick around her, and he rests his chin on her shoulder, “‘M glad we’re going on honeymoon tomorrow. I need a fucking break.”

“Are you okay?” She asks because he starts to worry her.

“I’m better with you here, yeah,” 

She can hear him smile a little and he places a kiss on the top of her head as his hands go around her hips. He maneuvers her around on his lap so she’s straddling him and she scrambles to get off, but he holds her in place.

“Dean, someone could walk in,” Her hands are braced on his chest and she looks into his face to find a grin, bright and wide. 

“No one dares to come in here, and you know it.” He whispers and pecks her lips. 

That’s true. Nobody ever goes near his office unless he’s calling for them to meet him. But still, she thinks it’s a little more than inappropriate to be sitting in his lap in his office when he is her fucking boss. “Still, we shouldn’t,” She says, and tries to get away but she’s weak herself, her body wants to stay, too.

Dean cradles her face with one hand, paints his thumb along her bottom lip before he pulls her close by the back of her neck, kissing her soft and deep. She hates that she loves it. Loves his kisses. They make her weaker than she already is.

She’s getting awfully wet down there and Dean’s getting hard, she can feel the friction of his bulge against her pussy.

“Your pants,” She says as a warning because she doesn’t really necessarily want to ruin his pants with how wet she is. 

He chuckles against her lips, kisses her once more, hard and demanding before he parts. He rests his forehead on hers, “You could take them off,” His hand goes to her breasts, kneads it through the fabric of her dress, fingers pinching at her nipple until they peek which in turn, makes her arch her back and drive her cunt harder into Dean’s hard cock. 

“We can’t do that,” She whispers, because they really can’t, can they? “Or can we?” She adds. Doesn’t really know why she adds it, but oh god, it feels good and fuck, she’d be lying if she wouldn’t want it.

Dean grins, it’s all cocky, “I want you to,” 

“But—” 

He kisses her harder, deeper, making her moan into his mouth and he sucks in her tongue, making her forget where she is. Her hands work on his belt buckle and Dean pauses the kiss, their noses touch.

“That’s my girl,” He coos, and that’s not fair. He has no idea what the praise does to her. 

Her hands work swiftly on his belt, and Dean’s hands are cupping her cheek as he kisses her over and over. He groans into her mouth when she grabs his hard cock in her hands. Her thumbs trails around his tip, smearing the drops of precum around his slit and over the velvety head. 

“Fuck,” Dean groans, presses his lips on her as he stands up from his chair, with her still around his middle, “I gotta—”

He doesn’t even care about the contract on his desk because she lays her on top of it, only swiping at the plastic cup of coffee, sending it to the floor. She can smell the spilled liquid. 

Dean lowers her onto his desk, kisses down her jaw, sucks in the sensitive patch at her throat, “I know I said I would take my time, but, fuck—” He kisses her again, “I need—” 

“It’s okay,” She grins, her hand finds his hair, fingers threading through the fluff on top of his head. 

His hands are restless, kneading and stroking along her legs and thighs, and he moans when his fingers find her panties and notices how wet they already are. One of his long fingers hooks around the crotch of her panties and she gasps when he threads two of his thick fingers through her bare and slick pussy lips. 

Dean leaves her neck to stand up straight, his hands grab her by her knee, folds them up. Her glistening wet cunt is now bare to him. 

“Jesus, look at you,” He mumbles, his eyes are dark, his lids heavy.

“Have you ever fucked someone in here?” She asks, but she doesn’t really know why she did, kind of regretting it immediately as soon as the words left her lips because she actually doesn’t want to know. 

He chuckles lightly, bends down to kiss her cunt, tongue parting her folds and lips sealing around her clit. He lets go with a loud obscene smacking sound before he comes up again and licks at his lips before he speaks, “Couldn’t help myself,” His breathing is ragged, “I just fucking love how you taste,” 

Dean lines himself up with her pussy and she bites on her lips when he pushes in. There’s the familiar stretch and she’s slowly getting used to it. Slowly getting fucking addicted to it.

“Oh god, fuck—” She closes her eyes and Dean leans down as he pushes himself deeper. His face is next to hers, his breathing hot against her ear.

“No,” He whispers, and at first she didn’t know what he was talking about until she realizes that it’s the answer to her question, “No, I haven’t.” He picks up a steady pace, fucks into her deep and slow, “But I always fantasized about bending you over and fucking you on this very desk.” 

He fantasized about doing this? About doing it with her? Doing it to her?

“Dean—” She starts to say but Dean claims her mouth, his tongue goes in as deep as his cock does, throwing her thoughts all over the place. He fucks her harder, sending the desk skidding along the floor. And she’s so close, so fucking close. 

“Christ, you feel so fucking good, I can never get enough of it,” He sucks at her throat before his tongue trails a hot and wet path to her mouth to kiss the corner of her lips, “Can you come for me, baby? Be a good girl and come on my cock, huh?” One of his hands goes to her clit, fingers rubbing circles on her little hood.

_ Shit. _

What is he doing to her?

“Ye-ah,” She manages to stammer.

“Yeah?” Dean nose touches hers and he chuckles, “Do it, baby, come for me,” 

That last baby she hears out of his mouth does the trick, she’s convulsing around him and Dean has to hold her thighs apart so as she wouldn’t crush him. Her eyes cross for a brief moment before she has to close them because of the pressure. 

Oh god, what does this man do to her?

Dean chuckles and leans down, sprays kisses on her face when she comes back down from her high, “Feels so fucking good when you come around my cock.” His voice is strained and she knows that he’s close, too.

But before Dean could come, they could hear screams outside in the hallway. 

Someone’s yelling. 

Sam. 

And then she hears Ruby who was exceptionally loud.

“Miss Shurley! You can’t go in there!” That’s definitely Ruby. She hears some footsteps, they are coming closer and closer. So many footsteps. Oh god. And she’s still here spread on his desk and Dean’s still buried deep inside of her.

She can hear Sam, “Amara! Stop!” 


	12. CH12

What is happening?

Her eyes widen in horror and Dean’s expression mirrors hers. 

“Shit,” Dean scrambles up to pull himself out of her, helps her up and there’s nowhere for her to hide and there’s also no fucking time, because the door’s already opening and the only sane thing they can both come up with, which is still fucking insane, is to push her under his desk while he sits down and pretends to be busy with the papers. 

When she crouches down and disappears, Dean rolls his chair closer to completely hide her down there.

Amara’s footsteps are clicking loudly on the floor as she walks into the room.

Dean clears his throat, “Don’t step into the coffee,” He says nonchalantly, and then he adds, “Or maybe do, and slip on it, I don’t care.”

“Dean,” Amara says and Y/N can hear her walking closer to the desk. Her heart thumps in her chest. Amara sits in the chair across from Dean. Y/N’s so glad that she’s hidden by the dark wooden desk.

“Sorry, I couldn’t stop her.” Sam follows her into the room and closes the door behind him. 

“How hard did you try, Sammy?” Dean’s voice is stern.

Y/N can see that Dean’s cock starts to soften. No wonder, Amara can do that to your libido. She doesn’t feel like fucking anymore either. But she feels like teasing him. 

While she listens into their conversation with one ear (something about Amara still not wanting to give in under Dean’s conditions — but she would consider 29% of his net worth, which is one percent less than what she first wanted. The woman is a fucking joke), Y/N places her chin on Dean’s thigh and she hears him clearing his throat audibly. 

She places her hand on the other thigh, and can’t help but grin to herself. Her hands go up his leg, and Dean’s voice is different. Maybe a little higher?

She wraps her hand around his cock, making Dean jump a little in his chair. She has to bite on the inside of her mouth so as not to chuckle out loud. She then works his lengths in her hand, feels him hardening in her grip to it’s full size — which is so mouthwateringly impressive. His cock is still slick from her juices and she has to be careful not to jerk him too hard because she’s sure that they could hear it if she did. 

Y/N gets on her knees, and Dean spreads his legs for her, sinking deeper into his chair. It makes her smile. 

So, he’s into it as much as she is, then.

Her hand works his cock and holds it up by its tip, before she presses her lips to his balls and starts to suckle him there. Tongue swirling around one ball and then the other. She takes one of them into her mouth and sucks at his skin, before she licks up the underside of them, feeling the heaviness of them on her tongue. 

“Fuck,” She hears Dean mutter under his breath but he’s quick go conceal it with a cough. 

She works the tip of her tongue up his shaft, until she can seal her lips around his cock head and she bobs her head a little. Not too much — just enough to not make too much noise. She works the rest of him with her hand, strokes him up and down, while her lips are sealed around his tip and her tongue is playing with his sensitive string. He still tastes of her. It mixes with his own musk, it’s salty and earthy on her tongue.

“Jesus,” Dean curses under his breath and she doesn’t really know if it’s because of her or because someone said something offensive. 

“Dean, you okay?” Sam asks and she has to chuckle with his dick in her mouth because she’s a little proud that she was the one who could make him lose his composure a little.

“Yeah,” Dean breathes out heavily. 

She hollows out her cheeks and sucks some more, her hands working faster. With every downstroke she can feel his balls draw up. He’s close she knows, because she can also feel the twitch of his tip and his cock is so much harder and hotter in her grip. 

Dean lets out a growl and he begins to cough above her while his legs tremble and they are caging her in, holding her in place as he empties himself warm and sticky into her open mouth. She almost couldn’t swallow it all, almost has to fucking cough and there’s cum running out at the corner of her lips down his shaft. 

Y/N comes up for air, swallows it all down, lets it warm her throat before she licks at the spilled cum up and down his shaft. She makes sure to clean him thoroughly. And when she finishes, she pauses and sits back to admire her work. 

One of his arms goes down to his cock, his fingers wrap around the base. She knows that he wants to tuck it in but it’s so hard for him to do it one handed without raising too much suspicion. And she can’t help him either because the clinking of the belt would give away her hiding place. 

Dean leaves his hand on his thigh though, and she can still hear them talking. Sam is explaining something to Amara and the argument is heated.

He pats his lap and she goes closer, lays her head next to his cock that is still half hard. How does he do that?

His fingers trail along her cheek, thumb caressing her lips and she can’t help it, has to open her mouth to twirl her tongue around his thumb. Dean’s whimpering above. 

Her hand takes his, and he let her, let her open his hands and spread his fingers. She sucks two of them in and Dean pushes the pad of his fingers down onto her tongue. He goes in deeper and she has to be careful not to gag. 

There’s another groan when the tip of his nails hit the back of her throat but she quickly pulls his fingers out because she’s not sure that she can keep going deeper without making a gagging noise. 

“Fuck,” Dean mutters under his breath. 

She places a kiss on the back of Dean’s hand before she sits back further away. Doesn’t want to disturb them anymore because she thinks that if she keeps on teasing him, this meeting will not be over before Dean will have to go to his next meeting and it’s hard for him to stand up when his dick is still out in the open.

“I can not go lower!” Amara hisses, “If I go lower than 27% we’re right where I was when this all started!”

“25% not enough for you, huh?” Dean snickers, “Amara, come on, I don’t know what you did — and you definitely did something because I wouldn’t marry you if you were the last woman on fucking earth — but the marriage in Vegas? That’s fucking not legal. I’m already married!”

“You didn’t sound married when you agreed on marrying me, Dean. You even wanted to pay extra to have more Elvis attending the wedding!”

“Well, that sounds like him,” Sam chuckles.

“Sammy, really?” Dean snarls at his brother.

“Fact is, we’re married and I know that your other marriage is fabricated.” 

“And you know that how?” Sam chimes in.

“Oh, please! He was seen with his arms around another girl, a couple of days before he got married? How do you explain that? Or maybe your wife is really a fucking idiot for not seeing that you’re fucking everything with legs on high heels.”

Dean’s legs shake. She knows that he wants to get up and slam his fist. But he can’t because his cock’s still out. “Don’t you fucking dare come in here and insult my wife.”

“Isn’t it true, though?” Amara asks. 

Well, Amara’s not wrong. Dean took someone out a month before she agreed to be his wife. Thanks for the fucking reminder, Amara. She didn’t need it. Doesn’t need to be reminded that she’s nothing special.

“It’s not.” Dean says, his voice is exceptionally calm. 

“Ha!” Amara laughs, “Well, let’s put it like that. I won’t agree to it unless you pay me out.” 

“Listen,” Dean gets a little louder but he’s voice is still composed, “I will find out how you tricked me into marrying you and then, Amara, you’re fucked, because Chuck will serve your ass on a platter for the shareholders, and you have to give up everything you own because that’s going to be mine. I’ll sue you for all you’re worth.”

Y/N can’t see Amara’s face but she can hear her breathing. It’s a loud snort and picks up in pace. She’s clearly upset. Instead of saying anything though, she stands up so fast, she sends the chair skidding across the floor. It’s a shrill sound and Y/N has to squint her eyes. 

She hears Amara’s footsteps, hears her walking to the door and then she hears it close with a bang.

“Wow,” Sam says.

“Sammy, for fucking real! You should have fucking stopped her!” Dean’s hissing at his brother.

“I tried!”

“Yeah, well,” Dean balls his fist and slams it on the desk. It’s not as loud as it would be if he would be standing up, “You didn’t try fucking hard enough!”

“I’m sorry.” 

“Were you distracted, huh? Did Ruby distract you?” 

Sam doesn’t answer.

“Jesus, Sammy. Next time Amara’s here, lock her in your office and don’t fucking let her near mine!” 

“Well, how do you wanna know if she really tricked you into it? Didn’t you just have too much to drink?”

The question makes her uncomfortable. In fact, the whole conversation makes her uncomfortable. She feels like she’s eavesdropping, which she is. But she can’t go out now. Sam will know and she’d rather nobody knows. 

“I’ll have dinner with Chuck tonight, maybe he knows something.” Dean says. He rubs at his scruff, she knows because the sound she hears is familiar. 

“How do you know that he’s really on our side?” 

“I trust him. I know. He hates her as much as I do. Maybe even more.”

“Alright,” Sam says, pats his knees and he stands up to walk to the door, “Oh, and, you can tell Y/N to come out from under the table.” 

She doesn’t see Dean’s face but she can imagine that his eyes widen at Sam’s remark. 

How does Sam fucking know?

“How—”

“I’m not an idiot, Dean. Tell her hi from me, alright?”

Dean doesn’t say anything, waits until Sam’s out of the door, waits until the door closes behind his brother.

When it’s safe, Dean rolls his chair back and grabs her by her arm, pulls her out and back into his lap to kiss her roughly. He probably still tastes himself on her tongue. 

“You’re unbelievable!” He kisses her again, sucks her bottom lip into his mouth to release it with a popping sound, “Almost got us fucking caught.”

She grins and raises her eyebrows, “Admit it, you liked it,” 

“Fucking loved it,” Dean chuckles, presses his lips hard to hers, his hands spread on her ass cheeks. 

“Mr. Winchester! You can’t go in there!” Ruby’s voice is loud and shrill.

“Oh, for fuck’s sake!” Dean curses under his breath and he pushes her down again, rolls his chair close so she would be hidden by him. His dick is still out. 

She hears the door opening and closing and then she hears heavy footsteps that walk closer to the desk. There’s slamming of papers and she can hear the deep voice of John Winchester.

“What the fuck is this about, son?” He shouts, “You married? You fucking married without telling us? You can be glad your mom’s on freaking vacation or else she would rip you a new hole!”

“What do you fucking care?”

“I heard she’s your assistant? Think about the business, son! Is she even good enough for you?”

“For fuck’s sake what is it today? Why does everyone have to walk in here and decide to fucking insult my wife?” Dean rubs around his scruff again, she can hear it.

“Is she your assistant or not?”

“Yeah, and? What’s your fucking point?” Dean’s even more angry than he was with Amara.

“Business and dick does not fucking mix! For God’s sake!” 

“I think it’s none of your business.” Dean’s voice is steady and loud.

“Of course it is! I still am a fucking shareholder I still hold fucking 15%!”

“Dad, seriously, she’s the most amazing girl, you’d love her if you met her.”

Okay, maybe her heart thumbs a little faster in her chest now.

“And where is she now?” 

“She’s in a meeting.” Dean’s an awfully good liar, she has to give him that.

“Well, take her to see us when your mother is back. We want to meet the girl who could make you settle down.”

“Sure. We’re going on honeymoon, though. So you’d have to wait.” 

“Oh, we will,” John says, and with that, he’s out the door without even saying goodbye to his son. 

When John’s out, Dean rolls his chair back and finally tucks his dick back inside his dress pants. He lowers his head to look at her, “Come out,”

“No,” She knows it’s stupid but she really doesn’t want to. 

It was a bad idea to agree to be his wife, she sees it now. It comes with more baggage than she thought it would and she still has her own fucking baggage to carry on top of it.

“Don’t listen to him, alright? He does not control my life.”

“Sounds like he wants to.” 

“Well,” Dean chuckles, “That’s nothing. You should hear my mother.” 

“Ugh, no thanks.” She grimaces.

“Come out, you can’t stay in there forever.”

“Watch me,”

“Jesus fucking Christ, Y/N, come out or I will drag your cute ass out there myself.”

“Fine!” She says and pouts as she crawls out from under his desk on her knees. 

Dean helps her up on her feet and kisses her forehead, “Don’t worry about them, okay?”

“I try.” She says, and she really does. She can’t get it out of her head, though. Can’t stop thinking that Dean’s parents will disapprove of her being his wife. Even if she’s just his fake wife. She definitely didn’t sign up for this.

  
  



	13. CH13

They arrive at a restaurant where Dean often frequents for business dinners. Y/N has pulled out her nicest dress for the occasion. She realizes that she definitely needs to do some serious shopping if she wants to help Dean keep up the facade.

Dean takes her hand in his as they make their way from the car to the front of the restaurant. When they step in, the maître d’ comes surging forward, having recognized Dean.

The tall brunette woman is Lisa, and Y/N knows her too, since her reservation for Dean always goes through Lisa. She realizes, though, that Lisa’s also the woman Amara was talking about who Dean took to an event right before her and Dean’s supposedly wedding day.

“Hey Dean,” Lisa’s smile grows wider, it’s bright, she shows off her perfect teeth.

“Lisa,” Dean greets her with a courtesy nod.

“Oh, hey, Y/N,” It’s only now that Lisa notices her. 

Y/N nods, “Hey, Lisa,”

“How are you doing, Dean? Haven’t seen you for two weeks. I already missed you!” Lisa turns her attention completely to Dean and ignores Y/N’s existence.

Dean lets go of Y/N’s hand and she thinks that he’s abandoning her. But then she feels his arm around her back, his hand around her waist as he pulls her closer to him, “Yeah, been busy, wedding and all,” He places a kiss on Y/N’s temple.

Lisa’s eyes widen and she looks at Y/N, her gaze resting on Y/N fingers with the diamond ring and wedding band.

“Oh,” Lisa breathes out and Y/N can see that the woman lost her balance for a second. She’s quick to compose herself, though.

“We’re meeting Mr. Shurley,” Dean says and Lisa types something in on her computer. 

She’s quick to look up again, “Your party’s already here, follow me, please.” There’s a smile on Lisa’s face but it isn’t for Y/N’s eyes to see. She notices it nonetheless.

If Dean notices Lisa’s hostility against her, he doesn't let on, carrying an easy conversation while they are walking to the back of the restaurant. 

When they arrive, Chuck smiles at them and greets them. There’s a blonde woman with Chuck who he introduces as his wife, Naomi. 

Dean pulls out a chair for her before he sits down himself. Lisa brings out the menu and hands it to them, before she leans down and whispers something into Dean’s ear. Dean’s laughing at Lisa’s remark.

Y/N pretends not to notice. She also thinks that it shouldn’t bother her— but it does. 

Chuck and Naomi are quick to strike up a conversation with Dean. Apparently Naomi is the CIO of Chuck’s company so the three of them have plenty to talk about. She feels a little left out, so she pretends to look at the menu, but her appetite is gone. 

Lisa appears with the wine Chuck ordered before, and she lingers a little longer around Dean. There’s some weird feelings in Y/N’s stomach and really, all she wants to do is to just stand up and leave. She doesn’t know why she needs to be here in the first place. They’re leaving for Jamaica tomorrow and she should be packing. Or... go drinking. Or…  _ the fuck does she know! _

All she knows is that Lisa usually works the front of the restaurant, but she must have switched with another waitress because that woman is swarming about their table. When they all clink their glasses, Y/N’s quick to empty hers in one go. She doesn’t really care about etiquette anymore.

Chuck and Naomi are talking and Dean sends Y/N a side eye when she signals for Lisa to refill her glass. He clears his throat but tries to follow what Chuck says. She likes Chuck. Because Chuck carries on as if nothing’s happening. As if she’s not having a silent meltdown right in front of Chuck’s fucking eyes.

Y/N empties her glass again, winks for Lisa to refill it a third time. If Lisa thinks it’s weird that Y/N’s already on her third glass while the others have barely taken a sip, she doesn’t say anything. Why should she. She’s here to work — and flirt with her fake husband. It might come in handy for Lisa if Y/N’s drunk. 

_ Oh my god _ , she’s jealous. She’s jealous when she shouldn’t fucking be.

“Baby, don’t you think you should maybe eat something first?” Dean says, his voice rolls smoothly above the chatter around them.

_ Baby. _

Ugh.

How dare he use it now.

_ Don’t you think that it’s none of your fucking business?  _ Is what she thinks, but doesn’t say.

Instead, she stands up, and sends a smile towards Chuck and Naomi, “Please excuse me,” She sends them a courtesy nod, for good measure, and walks out to find the bathroom. 

It’s a big restaurant, alright, the bathroom is in the basement and she needs to take the stairs. She clutches to the railings, and descends slowly, doesn’t want to miss a step that would most probably send her tumbling down.

“Y/N!” 

_ Oh, no. _

Dean.

He’s quick by her side and weaves his arms around her to walk back up the stairs with her again. Damn his fucking long legs. 

“What are you doing?” She hisses in a low voice, and adds, “I need to pee!” 

“No, you don’t,” Dean whispers while he grins and nods at a couple in passing who he probably knows. 

“How do you know?”

“You just went before we left,” 

Ugh. She hates that he knew about her plan to stay in the bathroom long enough to look at some cute pet videos on youtube. She needs a distraction so badly.

Dean guides her to the front and out of the restaurant but that’s apparently not enough because he walks her around the corner into an alley too. She’s so close to punching him in the crotch and running away, that’s how upset she really is. But what upsets her more is that she doesn’t exactly know  _ what  _ upsets her and  _ that _ is really upsetting. 

No, that’s not true, either. She knows why she’s upset. 

All her life, people made her feel like second best. It has always been like that. And her last relationship wasn’t any better. It wasn’t something impressive, since it was only a two months thing but she wonders if Dean knows about it. Wonders, if he knows about how Kevin cheated on her after only the first month and made her out to be the problem. Made her out to be the reason why he cheated and told her that’s her own fucking fault that he did. Made her out to not be worth Kevin's time or effort. It was too long ago, but she still remembers it as if it was yesterday. She remembers Kevin asking her to be his wife after only two weeks, and she foolishly said yes because she was naïve and way too young. Too young to know better, but now she does, and she has sworn to herself to not let anyone treat her like second best anymore, and also not to fall in love so fast, for that matter. Yet, here she is, fake married to a rich dude who probably won’t see her worth either. What’s the phrase? Fool me twice, shame on me? Yeah, it is all probably on her.

When they are out of sight and earshot, Dean lets go of her and paces around. He’s clearly distressed.

Good. Welcome to her fucking world.

He stops his pacing to thread a hand through his hair, “Can you tell me what that was all about? What’s the matter?”

“Nothing,” She says. It came out more calmly than she thought it would. Feels a little proud of herself.

Dean snorts, “Oh, don’t give me that, alright? When women say  _ nothing _ it means that everything’s wrong!”

Oh, look. He learned something through the years.

She crosses her arms over her chest, “Go in, Dean, find an excuse for me. I want to go home,” 

There’s no answer, just a glare, so she goes on, “Oh, and while you’re at it, maybe Lisa can take my place? I’m sure she’d be happy to.”

There’s a laugh that rumbles out of Dean’s mouth. It comes from deep in his chest, and she stares at him, waits until the moment is over. He walks closer to stand just right in front of her, “Is that what it’s all about? You’re upset about Lisa?

_ You mean, if I’m upset that Lisa makes her think that she was there first? Yeah. You bet’cha. You mean, if I’m upset that I’m falling for you? Hell yes! _

She bites her lips before she speaks, “No,” Her gaze is trained downwards.

“You’re a terrible liar, you know that? Always have been.” Dean stares at her. She can’t really see it but she can fucking feel it. His gazes are always so intense. And how dare he think that she’s a terrible liar? Which is sadly true, but still...

“What does it matter?” She sighs, and really, she doesn’t even know why she’s still here.

“Your wellbeing matters, alright? To know that you’re okay, it matters to me. So, what the fuck is wrong?” He isn’t necessarily loud, just really stating his point.

She rolls her eyes and sighs, “I don’t get it, Dean. I just don’t get why I have to be here. I don’t understand why you wanted me in the first place,” 

Dean’s hand reaches out, fingers skimming over her cheek, “You’re my wife,”

“That’s the thing? Why me, Dean? Wouldn’t someone else be the better choice? Maybe Lisa, because she’s the one you took out a couple of days before we were supposedly married? She would have been the better cover for you.”

“You’re jealous,” There’s a smirk on his face. How dare he smirk now.

“‘M not,”

“Sure,” 

“Amara was right,” She whispers, still not looking at him, “I look like an idiot because you dated before we married. What girlfriend would let her boyfriend go out to an event with someone else? It makes me look fucking stupid!”

“What do you want me to say? You want me to tell you that I’m sorry I took a waitress out on a date when we weren’t even a thing?”

Well, they are still not a fucking thing now, are they? Of course she has no place to be upset. She fucking knows that! They weren’t anything but boss and employee.

“I don’t know! I just—” She lets out a frustrating sound that comes out of the depths of her throat. 

Dean chuckles.

It makes her madder.

He comes closer, places a hand on the back of her neck and draws her closer, “I picked you, alright? And I told you already how happy I am that it’s you. I took Lisa out to a freaking award show, yeah. But that’s in the past. I don’t think she was by my side after we’ve taken the pictures at all. She went off to meet celebrities.”

“Did you fuck her?”

Why is she asking questions when she really doesn’t want to know the answer?

Dean frowns but it’s a playful frown, a smirk hiding at the corner of his lips, “Does that matter?”

“It doesn’t,” She sighs, because it really doesn’t, but still, “It’s just— She’s looking at me with eyes that says that she had you first and shows no respect whatsoever towards your wife.” She pouts.

“You’re cute,” Dean chuckles, “Look at me,” She reluctantly lifts her face and he smiles at her before he kisses her swiftly. He parts after, leaving his forehead on hers, “I didn’t fuck her, if you really want to know. And about that other thing, let’s go in and show her what she’s missing out on, huh?”

She doesn’t answer him, still debates with herself if she should go back in at all, because they’ve been out here for too long already and the others will look at her strangely.

“Please?” Dean says, tilts her chin up with his hand and kisses her again. 

Damn him. He knows that it's hard for her to resist his kisses.

“What did you tell Chuck where I went?”

Dean takes her question as a cue that it’s okay for him to walk her back, his hand is firm around her waist, “Told them you were stressed,”

“Why?”

“Because we have a pregnancy scare and we don’t want kids. Told them that you’re anxiously waiting on your period to arrive.”

“Oh, no,”

“Hey, just play along,” Dean shrugs and pulls her close to place a kiss on her temple before they walk into the restaurant again.

Dean’s true to his words, he constantly kisses her, nuzzles his nose against her cheek, touches her thighs, her hands, leans in to whisper into her ear. He showers her with affection, especially when Lisa is close to their table. And apparently it works because by the time their main course arrives, Lisa went back to the front of the restaurant.

“So Y/N, have you met my sister today?” Chuck asks and Naomi visibly rolls her eyes. Apparently, nobody likes Amara.

Her cheeks start to burn up. How can she tell that she hasn’t met Amara because she sucked Dean’s dick under his desk?

“She hasn’t,” Dean answers for her, and she’s thankful for that, “She was in a meeting.”

“Good for you,” Chuck smiles, “She can be a real bitch,”

Hah. She has to bite back a snort because that’s clearly an understatement.

“I think we’ve established that,” Dean says.

“My team is looking into leads that could help your annulment case,” Chuck smiles, “Which in turn would help my case,”

“Thanks, man,” Dean says and leans back, his arm goes behind her chair, fingertips stroking at her back, “I don’t fucking remember a thing,”

It’s the first time she hears about what happened. She didn’t dare ask before because it didn’t seem relevant to her.

Chuck chuckles lightly, “It is weird, you’re right. We had two tumblers of whiskey, nothing more. I remember saying goodbye to you and you walked to the other side of the hotel because our rooms were in different wings.”

“I don’t remember anything after that,” Dean rubs at his scruff with his free hand, “She must have put something in my drink.”

“We’re looking into it. Our company doesn’t condone it and she would drop out immediately.” Chuck says, his voice is reassuring and calm. 

Dean nods and bites on his bottom lip, “Yeah, I hope you’re able to find something,”

“Let us talk about something that will lift up our spirit, why don’t we?” Chuck grins, and looks over to Naomi who agrees with him. He turns back to them, “You’re going on honeymoon is that right?”

Dean’s face lights up and she tries to match his grin.

“Yeah,” He says, his hands play with her hair on her back, “We’re off to Jamaica tomorrow,”

“Who’s going to Jamaica?”

A shrill voice pierces the room. It makes all the hair on her back stand up.

“Oh, no!” Chuck rolls his eyes visibly and Naomi bites on her lips.

Amara struts over, dressed to the nines. It makes Y/N look like a bag of trash next to her.

“Yeah, we’re off,” Dean stands up, and holds out his hand for Y/N to take, “Chuck,” Dean nods, “Naomi,” another nod, “It’s late and we should get going. We still have to pack.”

Chuck nods back, understanding perfectly why they need to leave right now.

“See you,” Chuck says, and adds, “And I’ll get back to you on that... thing.”

“Would love to hear from you, man,” Dean says, and then he pulls her with him ignoring Amara who’s standing there like she’s the only thing that matters when all they did was to ignore her.

  
  
  


*

  
  


Back at Dean’s place, she walks straight to her room with Dean on her heels. 

When she opens the door, Dean holds her back by her hand, “Hey,”

She stops to turn around. 

He steps closer, his fingers slip underneath her chin to tilt her face up, “What can I do to get you into my bed tonight, huh?”

Y/N doesn’t answer straight away so he leans in, kisses her, soft and tender, his tongue brushing teasingly over her lips. When he breaks it off, she has to smile, “Well, that was pretty convincing, but no,”

Dean raises his eyebrows, “No?”

“Yeah, it’s just— so many things happened today and I have to process that,” She says, and adds, “Alone,”

“Okay, that’s fair,”

“And I’m still upset with you,”

“You are?” Dean frowns.

“Yeah,” She says but grins because Dean’s frowning some more, creases etched deep into his forehead, “I just need some alone time to gather my thoughts and I have to pack,” She honestly doesn’t know why she has to give him an explanation. It’s not like she owes him one. 

“Okay,” Dean says, he places a kiss on her forehead, leaves his lips there, “Be ready at 5am, alright?”

“Ugh, of course you’d take an early flight.” 

He has to chuckle at that.


	14. CH14

Y/N stirs awake when she feels something nuzzling against the back of her neck. One heavy arm drapes around her body and there’s a huff of hot air that brushes against her ear. She tries to open her eyes but it’s not going to happen. She feels like she barely slept at all.

“What? Do I have to get up?” She says groggily and finally she can get one eye to open up. The screen of the clock on her night stand shows her that it’s only 3am. She still has a little over an hour until her alarm would ring and why is she even awake in the first place?

“Shhhh,” A deep voice rumbles against her back, “Sleep,”

She yawns and turns around in his grip, cozies herself up against his chest. It took her some time to realize where she is and who she cozies herself up to, “Dean? Why are you here?”

“I don’t have an alarm yet,” He mumbles, his throat is right above her head, she can feel the vibrations on her forehead, is able to feel the bass deep in his chest.

“You have a phone,”

“You do too,”

“You can set the alarm on your phone,”

“I’m afraid that I won’t wake up,”

“Dean,”

“Shhhh,” He strokes her head, “Do you really want to discuss this right now or do you want to sleep?”

She doesn’t answer, instead she buries her face deeper into his chest and breathes in his scent. She likes smelling him and before she knows it, she’s falls back asleep.

  
  
  


*

  
  
  


They are on the plane, both of them breathing hard because they barely made it out here on time and she doesn’t really know who’s at fault because the bed was comfortable and she has had a hard time dragging herself out of the warmness of the sheets, plus she has had an awfully hard time untangling herself from Dean. 

The alarm went off at 4.15am and she woke up with Dean wrapped around her body. It took her a couple of minutes to remember him coming into her bed in the middle of the night, with a ridiculously lame excuse.

She didn’t want to get up at first and closed her eyes again. The next thing she knew the second alarm which she had set up went off, and it was already 4.30am. They had thirty minutes until they should be leaving so both of them scrambled up and put some clothes on to hurry out of the door.

Dean was grinning at her while he stood at the apartment door and waited for her to wheel her luggage out of his penthouse. She had put on her sunglasses, the lights of the apartment were too bright for her delicate morning eyes. 

“You’re definitely not a morning person,” He said and held the door open for her. 

On the way to the airport, she checked her phone to see that Ruby had texted her to tell her to have a nice trip. She wonders if the date with Sam went well, so she texted her back but Ruby’s most definitely still asleep — or something like it. 

While she packed her things last night, she texted Jack and he seemed to be on speaking terms with her again. At least there’s that. She has got to ask Dean if she can get a day off to go visit him once they’re back.

So now they’re sitting on tarmac and she’s a little nervous, can’t lie about it. She’s not a big fan of flying, and hasn't done it often enough to come to like it. The thought of being trapped in a confined space up in the air is kind of anxiety inducing. 

They are flying first class, which is a little over the top since it’s only a four hours flight to reach their destination. If she had a say in this, she’d have booked them coach, but really, she shouldn’t be complaining.

“You okay?” Dean leans in to whisper to her as she’s deep in thought and looking out of the airplane window.

She turns to him, a weak smile on her face, “No?”

He smirks and takes her hand in his, his thumb rubs circles on the back of her hand, “It’s going to be okay, don’t worry.” 

“How do you know? You’re not the pilot are you?” She grimaces, which in turn prompts him to laugh at her. 

“You can be glad it’s only a four hour flight and I’m not taking you to Bora Bora, which was actually my original plan.”

Y/N opens her mouth to say something but then her thoughts get derailed by the loud sound of the engines below her. They’re moving. Her hand clutches Dean’s and he changes his hand to let her grab at the other one while his arm goes around her shoulder to hug her closer to his chest. 

It’s not bad yet, they’re still rolling towards the runway. 

When the engine starts to get even louder, her whole body tenses up and she looks up to Dean. 

He’s smiling at her, as he starts to hum  _ Kokomo _ .

As if the humming is not enough, he starts to sing in a low voice too, “Aruba, Jamaica, oh I want to take ya,”

She has to roll her eyes.

“Can’t help it,” Dean purses his lips to a thin line and smiles with his eyes, “Bermuda, Bahama, come on pretty mama...”

  
  
  


*

  
  
  


She fell asleep about twenty minutes after take off and Dean woke her up to ask if she wanted something to drink to which she sent him a glare. Even the flight attendant who stands next to Dean notices, because she quickly retreats. 

He smirks at her expression and folds up the armrest that divides their seats, “You are definitely the crankiest morning person that I’ve ever known.” He pulls her closer, letting her rest her head on his chest, hums some more  _ Kokomo _ to piss her off, but she’s actually thankful for the distraction. She closes her eyes, listens to the vibration of the bass of his voice in his chest.

The second time she wakes up, Dean’s typing away on his phone while one arm is still around her. He’s probably preparing emails to send out as soon as they land.

“You didn’t want to sleep?”

Dean takes his eyes off the phone to look at her, “Nah, I’m used to little sleep, unlike the cranky person next to me,”

She yawns and pushes herself up as she tries to rearrange her hair. It stands up in every direction. Dean watches her. 

After a while she simply gives up because there’s nothing to save. Her hair is all electrified and she doesn’t have a brush to even it out and make herself presentable, “Gah!”

“What is it?” He pulls his eyes from his phone screen for a second time to look at her.

“My hair,” She pouts and slumps back into her seat.

He has to chuckle at that and locks his phone, places it back into his pants pockets. He’s wearing jeans, which are a little tighter and it’s a weird look, mainly because she’s only seen him in suits, but it looks good on him. The pants are tighter than his suit pants, which is actually not bad at all. But again, Dean could be wearing a trash bag, she thinks, and he would still look fucking good. Of course she noticed that the flight attendants were swarming around their seats. More than they attend to other passengers.

Dean tries to help her right her hair, tucks some strands behind her ear and smoothes it down on her head, “You look beautiful,” 

She pouts some more at that, “Liar,”

“Prettiest cranky thing if I ever did see one,” He says and closes in, his soft lips brushing against hers. 

It builds up fast between them and she gives in, lets him kiss her rough, lets him suck on her tongue and bite on her lips. 

God, she’s addicted to his kisses.

The overhead voice tells them that they’re descending, but she doesn’t care because his tongue maps out the inside of her mouth.

She didn’t even realize that they’ve landed and Dean smiles against her lips as they roll along the tarmac, “The distraction worked,” 

“Oh so, that’s all a distraction, huh?” She furrows her brows and is about to pout again.

Dean pecks hers lips bruisingly hard, teeth tugging at them before he parts, “No, can’t wait to get there because I’m dying to fuck you,”

He parts with a wolfish grin and she can’t hide the red of her cheeks at his word.

  
  
  
  


*

  
  
  
  


They’re on their way to the resort. She has basically no idea where Dean takes her because Ruby wouldn’t tell and of course Dean didn’t either. Her phone pings as they are in the limousine that would take them to their destination. She takes a look at it. It’s a text from Ruby.

Y/N reads it and she chuckles to herself, feeling her cheeks heating up.

Dean, who’s engrossed with his own phone looks over to her, and she’s sure that he can’t miss the blush in her face. It’s definitely not because of the weather because the limousine is cooled down to a perfect temperature. He probably also couldn’t miss the grin on her face, and how she has to bite down on her bottom lip while reading it.

He raises his one eyebrow, “What are you looking at? A dick pic?”

“Yeah,” She answers with a playful smirk before looking up to see him frowning. 

“Really?” He scoots closer and tries to catch a glimpse of her screen. She quickly puts her phone away and Dean frowns some more. He’s hovering close to her and rests his head against her shoulder, his nose ghosts around her neck, “You know that you’re not supposed to see other people’s dicks, right?”

She chuckles as she places her hand on his cheek, the scruff scratching away at her palm, “Yeah, that’s right. I’m only allowed to see your dick, right? Maybe you should send me a dick pic?”

Dean snorts, “Yeah, right. I don’t think you need a picture of it. You saw it in real life and I believe that I’m quite memorable.”

“Oh my god,” She groans and throws her head back. Dean’s laughing, his lips connecting to her neck as he places a kiss there. There’s another ping of her phone and she takes a look, it’s a picture of Ruby and Sam in bed. Well, their private parts are covered, at least there’s that. She starts to giggle.

Dean nuzzles his nose further into her neck, “Come on, what’s that about?”

“Well,” She smirks, “If you really wanna know, and I want you to remember that you have specifically asked for it,” She’s laughing now, “Ruby sent me a detailed description of her night with your brother. And she sent me a picture, too.” She turns her phone so he can see.

He immediately sits right up again, blinks a couple of times, and pinches at his eyes with his thumb and index finger, “Jesus, I’m going blind!”

Y/N shrugs, “Hey, you asked,” And then she thumbs down to Ruby’s previous message, “She said, and I quote,  _ Oh my fucking god, Y/N, Sam is such a great lover. His cock is not only big but it’s tasty too. Not too veiny. He’s shaved by the wa— _ ”

“Jesus Christ, now I’m deaf!” He let his head fall back onto the headrest. 

“Don’t be so dramatic, I didn’t even get to the juicy bits yet.” She’s laughing.

Dean looks at her, raises one eyebrow, “It gets even worse?” He shakes his head as if he’s shuddering all over, “I regret that I asked.”

She reads the rest of the message again to herself and she can see in the corner of her eyes that he’s watching her. He reaches out, fingers playing around with the hem of her shorts. Blunt nails skimming over her thigh.

“Did you tell her about me? About my dick?” 

“What do you think?” She asks, with a cheshire cat grin and Dean’s jaw drops. It also looks like he’s been holding his breathing. She wonders how long he can keep it up. After a while she says, “Relax, Dean. I haven’t told her a thing.”

Y/N has to laugh when she sees him breathing again. 

  
  
  
  


*

  
  
  


The hotel manager shows them to their room and she lets out a strangled squeal when she sees it. She’s quick enough to clasps a hand over her mouth but Dean hears it nonetheless. He is full on laughing while he pulls her close to him by her waist as the hotel manager is explaining their room to them. She didn’t listen, she can’t with that view, and Dean sensed it. He leans down to whisper into her ear, “Go on, take a look, I’ll talk to the manager.”

She looks up at him, her brows furrowed. But when Dean nods at her, her face immediately lights up. She stands up on her toes and kisses Dean’s cheek before she wanders off, his hands and fingers hesitantly lets her go.

The space isn’t  _ big  _ big. It’s big enough, though. Dean definitely didn’t hold back on this fake honeymoon trip. They’re in a honeymoon suite bungalow right over the water. There’s a rectangle of glass flooring by the end of the bed and she can see the blue of the water. There’s a fish swimming away and out of view. 

One wall of the bungalow opens right up to the Caribbean sea and they have their own balcony with a sizable pool and a hot tub next to it. There are big lounger chairs and she could technically jump right into the clear blue water from their room if she wants to. Although it doesn’t look very deep, so she’d rather not. 

She lets the breeze mess up her hair some more as she takes in the view and breathes in the salty air. Maybe she should probably change into less clothing because it’s unbelievably hot and slightly more humid than what she's used to.

Taking out her phone, she snaps a picture of the view and sends it to Ruby. 

“You like it?” Dean comes up behind her, his hands next to hers on the railing, bracketing her in. He lowers his face, places a kiss on her shoulder, moving closer to the junction where it meets her neck and she smiles, tilts her head to give him better access.

Y/N smiles, “Yeah, thank you.” 

Dean noses at her jaw trails it up to her ear, and lets out a chuckle, “You’re welcome.”

“There’s only one bed, though,” 

He sucks in a little skin on her throat, nibbles at her flesh, “It’s a honeymoon suite. I can’t tell them to put in an extra bed. If you want I can rent out another suite just for you?”

“Nah, but promise me not to steal my blanket?”

He chuckles some more, “Promise,”

She turns around and presses her lower back into the railing, “Can I take a dip in the sea?” 

He moves closer so they’re nose to nose, “Baby, you can do whatever makes you happy.” 

“I can even do you?”

Dean grins against her lips, “Hey, I just said that you can do anything you want. And if doing me would make you happy, I’d be more than happy to help.”


	15. CH15

Dean left her to splash around because he had a business call coming in. Y/N was surprised, she never knew that he works on weekends. 

When she climbs up the stairs from the sea, she washes herself free from the salt water under the spray of the shower on the balcony, and slips into the pool. 

She can see Dean sitting on their bed with a laptop on his lap and a headset in his ears. He already changed into his swimming trunks so no video call, then. 

He’s laughing at a joke someone made and looks up. Their eyes meet. 

Getting out of the pool, she lies down on the sun lounger, letting her skin catch some rays. Her skin burns, but not necessarily from the sun. No, the burning feeling definitely comes from Dean’s gaze that followed her from the pool to the lounger. 

After a while she turns from her back onto her stomach. She closes her eyes, feels the ray of sun warming up her whole body. 

“Jesus, Y/N,”

She hears Dean’s voice from behind her, and blinks her eyes open. He sits down next to her. From this view she can see the creases his stomach makes when he sits. It doesn’t make him look less sexy, and  _ that  _ is totally not fair.

“You’re going to look like a lobster tonight and not a living one!” He sits down and she hears a squirt of a bottle before she feels his hands rubbing at her back, applying sunscreen all over.

“Mmh,” She sighs. It really does feel good.

Dean moves lower, works his hands over her lower back and then he moves her bottoms, pushing them into the crack of her ass to apply sunscreen on her ass cheeks. He takes more time there, kneads them roughly before jiggling them in his hands.

“Hey!” She laughs.

“What? That’s how I apply sunscreen,” 

“Sure,” 

He works down her thighs, getting his fingers between them and brushes against her clothed pussy. My god, she’s turned on by a simple touch. 

She hears a groan as he works his hand there, rubbing at her clit through her bikini bottoms, “Dean,”

“Right,” He clears his throat, and works down her legs to her toes.

When he finishes that area, he comes up again, applies more sunscreen onto her shoulders. He pulls at her bikini top, making it come loose. 

“Dean!”

“Relax, nobody will see,” He rubs his hands along the base of her neck, “Turn around,” 

He’s right. They overlook the big blue sea, there’s nobody close by. She turns herself around and lets him apply sunscreen to her chest. He pulls the bikini top over her head and drops it next to the sun lounger only to cup her tits in his hands.

Leaning down, he captures one of her nipples in his mouth and sucks at it. She arches her back at the sensation and a soft moan rolls off her tongue.

Dean takes his time with her other nipple too, while his other hand kneads and pinches her other breast and nipple. 

After what seems like forever, Dean comes up again and smirks, her nipples are hard and perky, “Right, gotta finish what I started,” He says, works some more sunscreen down her stomach and her thighs. To her surprise he didn’t touch her where she wants him most but she thinks it’s just a stupid game he plays. 

When Dean screws the sunscreen bottle shut and stands up, she can see the tent in his swimming trunks. He’s definitely not able to hide that. 

Smirking, she asks, “You are not going to enjoy paradise with me?” 

He lets out a soft chuckle before he sits down again, his hands stroking her cheek, “I got another conference call. I should be finished in about two hours, okay? Gotta wait til then,”

“Okay,” She pouts and he thumbs at her lips before he bends down, kissing her soft and sweet. 

“Maybe you should go into the shade, or at least out of my fucking sight.” Dean growls a little and smacks her thigh. 

“Why?” She turns around on her stomach and he can’t help but smack her ass, too. 

“You’re fucking distracting when I’m trying to close a deal.” 

She giggles at that and wriggles with her ass some more. Dean spanks her one more time before he leaves to go inside.

  
  
  


*

  
  
  


Two hours came and went and Dean’s still not finished. Deciding that she’s had enough of the sun for the time being, Y/N goes inside to take a shower. It’s slowly getting darker, so she closes the door to their bungalow because she hates to have mosquitoes inside. Although, she guesses that there won’t be a lot of them because they’re so far out from the beach and there’s a steady breeze going all the time.

Dean didn’t seem to notice her because he had moved to sit at the desk to face the wall with his laptop. Apparently, she really did distract him. He had ordered room service in the afternoon and made a reservation at a restaurant here in the resort for the first night, but if he doesn’t finish soon, she doesn’t know if they can make it there on time.

After her shower, she walks out in a comfy bathrobe. Dean’s still chatting away at the screen and typing up an email simultaneously. She takes a book out of her suitcase and plants herself on the bed, her back rests against the headboard. The mattress feels comfy, and honestly, she can’t wait to sleep in it. She feels a little tired from the travel and the sun kissed her skin enough to make it glow after she moisturized it.

Just when she was about to open up the book to where she left off, her phone pings. She takes it from the charger. 

_ R: [picture] _

_ R: Guess you’re a celebrity now, huh? Don’t ever forget me, alright? _

Y/N thumbs the message open. It’s a picture of her and Dean at the airport, not really a paparazzi picture because the resolution of the picture is not that high and she can see that someone took it sneakily.

_ Y/N: I am shocked they recognized Dean. It was so fucking early in the morning. _

_ R: Everyone would recognize Dean. _

Ruby’s probably not wrong. 

_ R: How’s Jamaica?  _

_ Y/N: Great. I’ve been in the sea already and Dean spent his afternoon on conference calls.  _

_ R: Sam said something about the deadline of closing a deal, poor you. He’s got to make up for it. _

_ Y/N: Yeah, maybe he will. _

_ R: [picture]  _

_ R: I’m at his apartment, still.  _

The picture shows Ruby’s face and in the back, Sam’s sitting lazily on his couch. She grins, is truly happy about their progress. 

When she’s about to type something back, Dean stands up to take his headset off, and he rubs at his ear. It’s probably itching like hell. She has the same problem when she wears a headset for too long. 

Dean stretches himself. He’s still in only his swimming trunks. She can see every muscle moving and twitching. It’s kind of a turn on, not going to lie about it. 

He lets out a loud groan before he looks over to the bed and notices her. His lips curve into a smile as he slumps his shoulders down and walks over to the bed. He crawls over to where she is lying and lays his head into her lap. 

“I’m so exhausted,” He mumbles into the fluffy bathrobe and she chuckles, her hand strokes at his head. 

“I hope it was worth missing out on a swim for,” 

He looks up from her lap, grins the boyish grin of his that she has come to like, “We have a reason for celebration,” 

“Is that so?” She lifts one of her eyebrows. 

“Yeah,” He nuzzles his head deeper into her lap, “Finally I can invest in that company I was after. Their chairman didn’t agree on the conditions on Friday but it seems like I could convince him.”

“How did you do that?”

He smiles again, “I’m just  _ that  _ good.”

She rolls her eyes at his cockiness. 

Dean turns in her lap, looks up to her, “What were you doing?” 

“I took a shower,”

His eyes widen, and he gasps all fake and adorably, “You took a shower without me?” 

“Well, you were busy, sir.” 

“And why were you grinning before?” He turns to his side, buries his face into her stomach and she strokes his hair once more.

“You didn’t notice when I was showering but you notice me grinning?”

He laughs into her bathrobe, it feels warm where his breathing hits, “Yeah, I always notice you grinning, or smiling, or laughing for that matter.”

“Ruby sent a text. There was a picture of us at the airport.”

Dean stills and looks up, “Already?”

Y/N thumbs over her phone to show it to him. Dean’s expression is unreadable. 

“I don’t like it,” He mumbles, “I mean, it helps the case but I don't like people snapping private pictures behind my back.”

“We’re not exactly private, Dean. I’m your fake wife for a reason.”

He doesn’t answer, he sits up instead and he’s thinking about something, she can tell by the way he looks at her. She decides to change the subject, and shows him another picture. The one of Ruby and Sam in the background. 

Dean snorts, “Tell her that Sam better fucking check his emails. He’s got work to do since I worked all day to close this deal.”

She types away, wants to send Ruby Dean’s exact words but before she could hit the send button, he takes the phone from her hand and places it on to her night stand, “Hey!”

“I didn’t mean now,” He grins and slots himself between her legs, still on his knees, and pulls at her legs until she’s lying flat on her back.

“No?” She asks, it’s her turn to grin cockily. 

“Nuh-uh,” Dean mumbles, his fingers working on the rope of her bathrobe. It’s barely held together so he has no problem opening it up. Dean swallows when he sees that she’s naked.

He gets back on his knees and leans over her, his hand cradling her face as he kisses her. And again, it grows from soft and tender to rough and hard, no other man has ever kissed her like Dean does. He kisses her as if he wants to claim her, as if he wants to dominate her, to make her his. And honestly, that’s all she wants at this very moment. 

Her mind doesn’t agree though because she realizes that they have a dinner reservation and they’re not going to make it when he keeps on kissing her the way he does. 

She breaks the kiss, and Dean can’t quite stop, sprays little kisses on her face, down her throat, “Dean, we’ll be late for dinner.”

Dean chuckles, pulls at the skin of her throat with his teeth, “I don’t know about you, but I’m about to have dinner.”

“Oh my god,” He’s so full of himself. Of course she likes it, but still…

“Baby, it’s the first time that I get to have you horizontal, you think I care about dinner?” He cocks an eyebrow before his mouth latches at her throat and kisses down a path to her chest. 

He flicks his tongue against one of her nipples, kneads the other tit in his big fucking hand and she writhes below him. Her hands fly to his head, fists themselves in his hair. Dean seals his whole mouth around her nipple, tickling it on the inside with his tongue and he uses his teeth too, making her moan out at the sensation and there’s something pulsing between her thighs but she can’t quite reach there because Dean’s blocking her fucking way. 

“Dean,” She whimpers, doesn’t care that it sounds needy because that’s all she fucking is. She squirms some more to make him notice. 

Dean chuckles and sucks in her nipple, only to let it out with a wet popping sound before his lips connect back to her body, and he licks his way down her stomach. He slots himself further between her thighs, and spreads little kisses along her pelvis, down to the apex of her thighs, leaving out her center on purpose and it’s fucking killing her. He’s such a tease. 

“Dean!” She’s louder, but she can’t help it. She’s dying here and he thinks it’s funny. 

“What?”

“Would you just—”

Dean licks his lips and grins at her before he thumbs along her center, parting her folds with both of his thumbs. He stares at her pussy and she feels a little uncomfortable. He lets out a low growl when he sees her glistening. She knows that she’s awfully wet. Has been since this fucking morning actually. 

“Tell me what you want,” Dean’s face is so close to her cunt, she can feel his breath hot against her center. 

“God, can you touch me there?”

“You’re too cute,” He chuckles but instead of teasing her some more, he gives in, licks a broad stripe up her center and seals his lips around the hood of her clit. 

Y/N fists her hands in the sheets, “Fuck,” 

“That’s the plan,” Dean mumbles against her slick folds, french kisses her cunt and groans when he feels her getting even wetter. 

They haven’t had  _ that  _ kind of sex before. It was passionate too, but mostly real quick and never horizontal. She can feel that Dean wants to take his time and that in turn, drives her fucking crazy. She also never had someone eating her out like Dean does. Her ex Kevin was okay with foreplay but he doesn’t really like it. He mostly licked her to get her wet enough to plunge his dick into her but that’s not the only point on Dean’s agenda. She can feel that he really, truly loves to eat her out, and he’s determined to make her come on his tongue. He doesn’t seem to mind if he would be down there for hours on end. It blows her mind.  _ He  _ is blowing her mind. 

Dean hums against her cunt, his scruff rubs against her thighs and she’s close because Dean sucks and his humming sends the right vibration against the nub of her clit. She pushes herself off the bed with her feet, driving her cunt deeper into Dean’s face and holds him steady with her hands in his hair. He doesn’t seem to mind, hums along, licks and slurps up his own drool and her juice. God, it sounds so fucking obscene and it turns her on even more. 

“Fuck, yes, yes, oh god, don’t stop,” She moans out and Dean shakes his head, hums some more. He changes between nibbling and sucking and it feels so fucking good. 

“Oh god,” Here it comes, she feels her thighs cramp up, feels her insides trembling, her walls convulsing and she can’t help but push herself harder against his face. Dean’s hands are around her thighs, holding on for dear life as she locks her thighs around his face, caging him in, when she comes. 

She pants hard when the moment’s finally over, laughing loudly and Dean taps at her thighs, asking for her to release her grip around his head. 

When she releases him, Dean looks up from below, his nose and lips are shiny from her slick. He smacks his lips loudly, swallows hard, “Good?” 

“Oh my god, yes,” She says, clasps her hand over her face. She probably looks like she just ran a marathon. 

Dean places one more kiss on her clit before he pushes himself away and stands at the foot of the bed. With one swipe, he gets rid of his trunks and climbs back to bed, walks on his knees up to where she is. 

He strokes himself, jerks off his impressive dick and he bends down, kisses her hard. She can taste herself off his tongue.

“Fuck— I—,” Dean’s breathing hard.

She grins up at him, takes his dick in her hand and begins to stroke him up and down. She gets on her elbows, and sticks her tongue out to lick at his balls, sucking them in one by one while her fists are tight around his tip, stroking up and down. Dean spits on the head of his dick, helps slicking his cock up while she worries at his sac, “Fuck, your mouth feels amazing,”

He lowers himself a little when he notices that she wants to take him further into her mouth, his hands stroking along her legs and thighs. She takes him in, tongue licking up along his shaft before she seals her lips around his tip. Dean lets out a groan when she takes him deeper, his hand rubs circles on her clit before he toys at her entrance, slipping in one finger and then two. He moves faster inside of her, making her hum and sucking him off harder.

“Baby, as much as I would love you to suck me dry, fuck, I— your mouths feels too good,” Dean pulls his dick away from her, takes his wet fingers out from her cunt and flips her over with no problem at all. 

Dean helps her get rid of her bathrobe, throws it somewhere in the room, “On your elbows and knees,” He says, his voice is low and it sounds strained. 

Y/N can’t lie, she likes when he tells her what to do.

Propping herself on her elbows and knees, she waits. Dean’s one hand is jerking himself off while his other one kneads at the flesh of her ass. He spanks down on one of them, she’s sure that her skin turns red immediately. Leaving his hand there, he jiggles her ass, “Fucking beautiful,” He whispers and then he lowers himself, she can feel his face between her asscrack. Dean tongues at her clit, licks up her rim to her asshole and she moans out shamelessly. 

“Like that?” His voice is cocky.

“Y-yes,” She admits and Dean takes the cue to lick some more. God, she fucking loves it. Never felt anything like it before. 

“Fuck,” Dean curses, “You’re so tasty, but I really gotta—” He holds his cock out, threads the head through her slick and rubs it against her cunt, teasing her. 

“Dean, please!” She’s damn near exploding. She wants him inside right the fuck now. 

“Yeah, yeah, I’m—” Dean mumbles and pushes his tip into her waiting and slick cunt. He rests the tip there before he places his hands around her hips and pushes in, groaning louder the deeper he gets. 

“Oh fuck,” She bites down on her lip, lowers her forehead to the mattress, “You’re so fucking deep,”

“Jesus, you feel so good,” Dean groans, his hands kneads her ass, pulling them apart to watch his dick go in and out of hot and wet heat, “Looks so fucking great,” 

He goes slow, before he picks up speed and while it’s perfect, she can’t help but want even more. 

“Dean, please, harder,” Y/N’s body is filled with want, and she fucks back into him. 

“Christ, look at you, so fucking perfect,” He spreads her ass cheeks wider, “Yeah, fuck yourself on my cock, baby, take what you want, good girl,”

She shakes her ass while moving back and forth, and she can hear him chuckle before he spanks down on her ass. The pain is sharp, it soars through her body. Not going to lie, it is painful but it fucking turns her on.

“You like that? Like to be spanked?” 

“Fuck,” She’s glad he can’t see how she turns red, “Yes!”

Dean lets out a groan at her answer, spanks her twice more, for good measure, “Jesus,” He pants and then he starts to set a fast pace, fucking in to her with wild abandon. 

At one point, he leans forward, grabs her by her arms and pulls her up against his chest, his one hand yanking at her hair while his other hand goes down to rub at her clit. He never stops fucking her hard, like she wants him to. 

“Oh god,” She moans out upon feeling her second orgasm approaching.

Dean licks up the shell of her ear and whispers, “Come, baby, be a good girl, come for me,” 

And that, she does, comes hard around him, her cunt pushes him out and Dean has to let go of her and pushes her down on her elbow again to be able to slip inside once more. 

“Fuck, you’re still coming, so fucking tight,” He has to bite down on his bottom lip at the tight squeeze. It needed only a couple more thrusts for him to come deep inside her and he leans down, sinks his teeth into her back before he sucks and licks at the mark he left behind. 

His legs gave out and he collapsed on top of her, and he turned them around in his grip so that he was spooning her from behind. They’re still connected. Dean has his arms around her middle, kisses along the nape of her neck to her shoulder, “You’re something else,” 

“Am I?” She strokes along his forearm. 

“Yeah,” He breathes out a chuckle, “I came so hard I think I blacked out.”

They stay connected for a while longer until Dean slips out with a squelching sound. He carries her into the shower and she finds herself showering for the second time. 

He dries himself off before he goes out to get the robe for her and comes back holding it out for her to step into, “How about we don’t go out tonight? We can order room service.”

Y/N agrees because her legs are too wobbly to walk anywhere right now. 

They’re cozy in bed with her lying on her stomach on the other end from Dean who has the cover pulled to protect his modesty while typing away on his laptop. They’re both still naked and she’s well aware that Dean has a clear view of her cunt and ass, but she didn’t mind very much. It seems like the most natural thing to be when they are around each other. 

Finally she gets to send out the text to Ruby and there’s immediately a reply back.

_ R: [picture] _

_ R: Sam’s working right now. _

It’s a picture of Ruby’s face and Sam’s in the background, staring grumpily into the camera. 

She has to laugh which prompts Dean to look at her with one raised eyebrow. She looks back and holds out the phone to show him the picture, “Sam’s working.”

“As he should,” Dean says sternly and she turns back, her thumb hovers over her screen. 

Y/N starts to type a reply when Dean closes his laptop and gets out from under the covers to come crouching on top of her. He’s already half hard again, she can feel the tip of his dick brushing over her ass. 

“You want to send her a picture back?” 

She frowns, she’s actually never thought about it but now Dean makes her second guess it, “I don’t know,”

“Come on, do it,” He nuzzles his nose against her temple. 

“What?”

“I know you’re good friends and she always sends you pictures. So maybe if you really want, you can send one too, I’m okay with it.”

Tilting her head to her side, she meets his green eyes. He’s smiling, the crinkles deep around the corner. 

“Really?”

“Yeah,” 

“I don’t know,” She is having doubts. It’s not like they have something going on like Sam and Ruby do. Their arrangement is purely business. 

“C’mon,” Dean takes her phone out of her hands, and holds it out to snap a picture, doesn’t even mind if they’re still naked.

His hands are longer than hers, it can snap up a picture from a wider angle. She sees herself on the screen, sees Dean behind her, his chin on her shoulder. Her hair covers her boobs.

Dean lowers his face, kisses and sucks at her shoulder while he looks up at the screen, the wrinkles on his forehead showing. She bites her lip because his warm tongue and sharp teeth feel great on her skin. He quickly snaps a couple of pictures. 

He gives her back her phone, urges her to send one out again when he nibbles and sucks at her throat. 

God, this man is doing things to her.

She quickly sends it out. Doesn’t even write anything else and abandons her phone because Dean turns her around, kisses her lazily soft. 

“Come on, we should get some sleep,” He whispers against her lips. 

“Why?” 

“Because I don’t think I wanna wake up to a cranky you again tomorrow.” He chuckles lightly, and gets off the bed to pick her up before he pulls the cover away with one hand and lets her fall back into the bed with the other. He climbs in after her, spreads his arms for her to crawl in. 

He kisses her again, all soft and tender. It’s a contrast to how he just fucked her. She likes both sides of him. Likes how he can go all rough and demanding on her but shows her his softer side as well. And it’s easy, she thinks, they are comfortable around each other, at least as far as she can tell. She just wishes that the circumstances around whatever they have right now would have been different. 


	16. CH16

The next two days went by too quickly for her liking. This place is truly magical and Dean really went out of his way and made an effort on making the fake honeymoon memorable for her. 

He had taken her on a snorkeling trip and they have things lined up for the rest of their stay. There’s still so many things to do and see. She really wants to see it all, and she’s especially curious about the waterfalls.

However, they still didn’t get out of the bungalow much because they were too busy staying inside. She thinks that Dean has probably fucked her all over the place and there’s no spot or surface that they haven’t christened yet.

Dean says that she’s too hard to resist, but actually she thinks that it’s the other way around.

On their third day, Y/N wakes with Dean spooning her from behind. They didn’t draw the blinds last night and the sun’s already high in the sky. They’ve slept in like this every morning since they’ve been here. Dean has slowly got used to sleeping for so long. She thinks that he’ll have a hard time once he’s back home again. 

She stirs, and winds herself around in Dean’s grip. He is still sleeping, his lips are slightly parted. He looks peaceful and content, his freckles stand out more than they normally do on his tanned skin. She could watch him sleep for hours, but there’s a knock at the door. 

Slipping out of bed, she drapes the bathrobe over herself and opens the door to a butler delivering their breakfast. He places the big tray on their coffee table and is quick to leave again.

Y/N pours herself a cup of coffee and drinks half a cup before getting back to bed. 

Dean stirs when he feels her beside him. He squints his one eye open, and there’s a frown on his forehead, “You’re wearing too much,” His voice is raspy, full of sleep. It’s also sexy as hell.

“Well, good morning to you too,” She smirks.

“No, seriously, lose the robe,” Dean mumbles, as his hand reaches out to tug at the collar of the robe. 

She hesitantly takes it off and Dean’s closing his eyes again but he’s grinning, knowing that he’s won. Sometimes, Mr. Winchester can be a little shit, and she hates that she likes him like that. 

He quickly draws her closer to him and spoons her from behind. She can feel his swelling cock poking at her ass. His one arm drapes over her, holding her tit in his hand and he nuzzles his nose against the back of her head, “Could get used to waking up like this,” 

Y/N’s cheek always flares up when he talks like this. Sometimes, his words make it seem like what they have is real, and she doesn’t really know what to think of it. She doesn’t want to get too invested. Does not want to get her heart broken. What she does know though, is that she’s trying to enjoy this as best as she can. 

Her phone chimes with a message and she gets out of his grip to reach for it to. Dean starts to whine at the loss of her in the bed, and he makes a sound of content when she goes back into his embrace. 

She unlocks her screen, sees the message from Ruby.

_ R: [picture] _

_ R: Hope your honeymoon is fucking worth it. We’re swamped here. I have to work through this today! _

It’s a picture of Ruby’s desk covered in papers. 

_ Y/N: Hey, don’t blame me. Blame the boss. _

_ R: Ugh, I know. I’m happy for you but I also can’t wait til you guys get back. You will get back, right? _

She chuckles, which prompts Dean to ask if someone has sent her a dick pic again. “Nah, just Ruby showing me all the things she has to do today.”

“Send her a picture of things you have to do today,” Dean suggests. 

“What?”

“Me.” He chuckles, satisfied with his own joke and she can’t roll her eyes to the back of her head fast enough, “I’m serious.” He grabs the phone from her hand and holds it up, and she makes sure that her boobs are covered by the sheets. Dean snaps a couple of pics with him nuzzling his face into the back of her neck and she doesn’t even look into the camera because she knows that she looks like shit in the morning. 

_ Y/N: The boss said I should send you a picture of things that I have to do today. _

_ Y/N: [picture] _

_ R: Fuck! I’m so jealous! Well, not with Dean but I’d like to do someone too. _

_ Y/N: How’s it going with Sam? _

_ R: Good, he’s taking me out tonight. I’m excited! _

_ Y/N: Dean’s taking me out tonight, too. Finally. _

_ R: What, you haven’t been out? Not even for dinner? _

_ Y/N. Only room service. We were kind of busy. _

_ R: Oh you little minx. Anyway, I need to get this done and you should do your… thing.  _

She grins and places her phone back onto the nightstand. Just when she was about to turn around to check if he fell asleep again, his hands wanders around her front, brushing along her stomach to cup around her pussy. 

Dean groans into her hair because she knows what he feels. He strokes along her folds while he rubs his now fully hard cock against her ass cheeks, “Fuck,” He slips in a finger, then another and she arches her back, drives her backside deeper onto his hard on.

Her pussy’s still so slick and full of his cum from last night, she’s sure that he can feel it too. 

“C’mon,” he whispers and pulls his fingers out, making her whimper at the loss. Dean maneuvers her over him so she’s lying with her back to his chest. Her lower back is on him while her shoulder blades hang down his body and rests on the mattress. He slips a hand around her shoulder, with his other hand, he lines himself up at her entrance before he moves that hand up to cup her around her chin, tilting her head to be able to kiss him while he pushes his cock up and into her. 

“Jesus fucking Christ, I love being inside you,” He whispers, kisses her jaw and her chin. 

“Shit,” She can’t really say anything else, it feels too good. She likes the thickness of him, likes how good he fills her up.

He soon picks up his pace, fucks up into her faster, and there’s something about the position that they’re in that brings her over the edge way too fast. Her legs cramp up and she shakes above him as she comes on his cock without even touching her clit. 

Dean’s lips are resting on her cheek, he pants hard, “So good,” Kissing up her face, he licks at her ear, “Such a good girl coming on my cock,”

His one hand is around her throat, keeps her pinned against the pillow and his arm, and her face turns to him as he applies a little more pressure. She gets light headed. Dean starts to fuck her harder, “You like my cock, don’t you? Like it when I fuck you hard and rough?”

Oh god, what is he doing to her?

“Y-yes— oh fuck—” 

He kisses her again, as rough as he fucks her, as hard as his fingers around her throat. And she comes again without any warning. 

Dean grunts, his hips twitches and his hands are trembling as he feels her pussy walls clamping down on him. He buries his face into her neck, bites and sucks at the junction where it meets her shoulder, and starts to shudder all around. 

“Oh my god,” She pants, and she hears him chuckle into her skin. He quickly turns her around to spoon her again without slipping out of her. 

He sprays kisses along her shoulder and back and she strokes her nails along his arm. She starts to chuckle and he asks her what’s wrong.

“I finished my to do list for the day,” 

Dean laughs out loud, the bass of his voice rumbles at her back, “I think my name’s on that list twice.”

  
  
  


*

  
  
  


For Y/N, the rest of the day was spent lounging around. Dean has another two hours of conference calls he couldn’t talk himself out of. 

He makes it up to her by booking a masseuse to come over and give her a massage while he is in the meeting. He deliberately locks himself in the bathroom to talk, so as not to distract himself while the masseuse kneads all the tension out of her body.

When the masseuse finishes, she lets out a deep content sigh and feels light all over.

Dean walks out of the bathroom to find her on the bed with a contented smirk on her face, “I feel like I should be the one to make you feel like this and not a masseuse,”

“Nobody can make me feel like this but the masseuse, don’t worry,” 

Dean frowns before he bends down to kiss her.

  
  
  


*

  
  


Dean wears his dress pants and a simple white shirt, sleeves rolled up to right below his elbow, two buttons loose around his collar. She opts for a simple dress in white, thinks that it goes great with her tan. Not that she doesn’t want to wear anything fancy. It’s more because she doesn’t have anything fancy and she feels bad asking Dean for shopping money, he’s already spent too much money to take her on this trip.

When she steps out of the bathroom, Dean’s lost in his phone but when he notices, he looks at her with that intense gaze that makes her stomach turn and her heart flutter. 

“You look lovely,” he says and licks his lips before he stands up to reach around her waist. He pulls her closer, and kisses her cheek. She’s glad she’s tanned, and her cheeks don’t flare up so fast anymore.

  
  


*

  
  


They arrive at the restaurant and the waiter shows them their table. Dean orders wine that goes down quite easily. It’s the first time that they have had dinner with just the two of them outside of their confined space, and it feels easy. It feels like there’s not a contract between them. She likes that easiness.

It’s after they had their appetizers that they heard a familiar voice. 

“My, my, look who’s here!”

They look up to see Amara, and Dean’s expression changes from easy to stern. 

Amara has her hand around the arm of someone and the waiter is about to show them their table when she suddenly says, “Oh, can we join you?” Before she turns to the waiter, “You know what? We like to sit with our friends.” She doesn’t even wait for their answer, sends the waiter away to set another table next to them and they cater to her wishes without even asking Dean who has his hands balled into fists. 

The people from the resort restaurant are quick to set up the table and Amara sits down next to Y/N.

“Y/N, you come sit next to me,” Dean’s voice rolls loud and deep above the chatter around them. It’s that authoritarian voice she normally only hears at work.

“Why? I think she’s perfectly fine next to me,” Amara smirks.

“I want my wife close to me,” Dean growls and Y/N scrambles off her seat, takes her wine glass with her. Because she wants that too, wants Dean close when Amara’s around.

When she sits down next to Dean, he quickly places his hand on her thigh as a way to calm her down, but he’s tense himself, she can feel it.

Amara introduces her companion as her boyfriend. His name is Arthur Ketch and his cousin is apparently some Duke from England. She gushes about him, as if Dean or Y/N would care.

So Amara has a boyfriend but she still doesn’t want an annulment. She doesn’t really understand Amara’s motives. It’s not like she  _ needs  _ Dean’s money. Amara has plenty herself.

“I see Dean still didn’t give you money for proper clothing, did he honey?”

“None of your fucking business, Amara,” Dean scoffs.

“I just think if you’re really married, you would want your wife to look presentable,”

“Not everyone is as shallow and greedy as you are,”

It’s a heated exchange between Dean and Amara and her and Ketch just look at each other, neither of them saying a word.

Amara’s really ruthless. She doesn’t back away and then she laughs, all loud and fake, “Oh, Dean, who are you to talk about greed? You’re the one who wants to help my greedy brother push me out, aren’t you? Well, too bad for you that I’m going to walk away with the money and there’s nothing you can do about it.”

“Dean,” Y/N whispers, tries to calm him down because she can see Dean’s lips twitch. He’s doing his best to hold himself back so as not to make a scene in a full restaurant. She moves closer to him, weaves her arm around his and lays her chin on his shoulder, “Look at me,” 

Dean’s gaze is still fixed on Amara and he looks more than pissed. 

“Hey, look at me,” She whispers again, waits for him to register her voice. He reluctantly tears his eyes away from Amara and slowly tilts his head in her direction. 

Y/N smiles at him when he finally looks at her. Her hand cradles his face and moves in to kiss his chin, his jaw, his cheek, moves up further to his nose and there’s finally a smirk on his face. She kisses his lips and Dean kisses her back, his hands on the back of her neck, pulling her closer into him. She breaks the kiss before it can get too heated, and she looks at him, “You okay?”

Dean nods, pecks her lips again, “Yeah,”

“We can go if you want, okay?”

He nods again, “Okay,”

Amara clears her throat audibly, “Ah, I almost believed that the kiss was real. You’re both too cute.”

Dean wants to open his mouth to protest but Amara cuts him off, “I talked to your brother, Y/N,”

“Jack?”

“Yeah, but his lips are tight. Wonder how much Dean pays him to stay silent. I bet I can get him to crack.”

“Leave my brother alone you stupid bitch!” She stands up so fast, it sends her chair skidding back and she thinks that everyone’s staring at her, but she just doesn’t fucking care. Jack shouldn’t be pulled into this, at all cost. 

“Baby, come on,” Dean stands up, “We’re leaving.”

“Awe, you didn’t even get to your main course!” Amara just doesn’t know when to shut the fuck up.

Dean takes her hand and leads her out of the restaurant.

  
  
  


*

  
  


As soon as they're in their bungalow, Dean makes a call to Ash, the company’s IT guy. 

“Yeah, sorry to disturb, Ash, but I need you to do some research. Name’s Arthur Ketch. Report everything you find about him back to me asap.”

He pockets his phone and walks to her. She’s sitting on the bed, still shocked that Amara is casually talking about her brother, that she talked to him when Y/N didn’t even have a chance to do it herself yet. 

Dean sits down next to her, wraps his arm around her shoulder and pulls her close to kiss her temple, “I want you to call Jack now. Tell him that I’ll book him onto the earliest flight we can get out here. Tell him that he needs to take some time off from college to come to Jamaica. I don’t trust Amara, I need Jack here. I wanna be able to explain it to him. Is that okay with you?”

“Yeah, sure,” She nods. She wants that too. Wants for Jack to be here where she can keep an eye on him. 

Dean kisses the top of her head before he gets up to call Sam and Y/N calls Jack in the meantime, waking her brother up. To her surprise, he sounds thrilled about taking a trip to Jamaica. Which is understandable, really. The last trip they made was two years ago, when they went to visit their aunt in Canada. 

She still sat in the same spot when Dean comes back to sit next to her.

“Ruby’s booking the flights right now,”

“Okay,” She nods. 

“Are you hungry? We could order something, we didn’t even get to the main course,”

She shakes her head, “I feel nauseous,” 

Dean chuckles weakly, “That always happens to me when I see Amara.”

  
  
  


*

  
  
  


Once they calmed down and sent Jack his itinerary, they got ready for bed. 

Dean slips in beside her, pulls her into his chest, and she breathes in the now familiar smell of him. He strokes her hair, cups her cheeks and tilts her head to place a kiss on her lips, “Don’t you worry about it, okay? We will talk to Jack and explain everything. Soon, this will all be over and you can go back to your old life. Jack can finish his degree. I’ll help you pay it off. You can use your money for other things, maybe buy more sappy books,”

She punches his chest and Dean lets out a chuckle before he kisses her forehead.

“Sleep, okay?”

“Okay,” She says. 

But what she actually wants to say, but doesn’t know how, is that she doesn’t really want to go back to her old life. That she wants to be like this, with him. Wants to wake up to him next to her. Wants to feel his lips on her skin, wants to feel his hands on her body. She fucking wants him, and to know that she can’t, really breaks her heart.

  
  
  



	17. CH17

Y/N wakes up the next day with Dean already out of bed. There’s a tray of breakfast propped on the coffee table. She didn’t even hear the knock at the door when someone brought it. Sleep was bad. It took them both a long time to fall asleep and then she kept waking up during the night. 

She blinks the sleep away and sits up in bed. Looking out, she sees Dean. He’s talking on the phone and has gone outside so as not to wake her up. Still feeling tired, she lets herself fall back into the mattress and buries her face into the pillows before pulling the covers over her head. Maybe, if she’s lucky, she can fall asleep again. 

There’s the sound of a sliding door, and she hears Dean walking back in. He probably has noticed her moving, and took it as a sign that she’s awake. 

“The others will arrive in an hour, you think you wanna get up?”

Well, there goes her sleep.

She peeks out from under the covers and sees Dean sitting next to her on the bed, “The others?”

Dean scoffs, “Yeah, I’m not happy about it either, but apparently Sam and Ruby are seeing it as an opportunity to have a short vacation with the false pretense that he’s my lawyer and he needs to be here to discuss  _ strategy _ .” He air quotes the word strategy.

“Ruby?”

“She’s coming because he probably wants to impress her,”

“As if he has to try,” she chuckles, and adds, “Are we picking them up?”

“Nah, Jack’s in good hands. Ruby made sure that Jack was on their flight.” Dean’s hand goes under the covers, grabbing her around her waist and pulling her to the edge where he is, “So, you still have time to take a dip in the sea if you want to? I need to go to the front desk and arrange a room for your brother.”

“Not for Sam and Ruby?”

“I think they can manage on their own,”

Y/N smirks, “Can we stay in bed for a little while longer?” 

Dean has to smile at that, “Okay, ten more minutes,”

She scoots over again and he gets in, nuzzles his face into her neck while he drapes his arm over her body. 

  
  
  


*

  
  
  
  


Ruby hugs her so tight, she has trouble breathing but who she was most excited to see is Jack. 

“Hey,” Jack smiles weakly, visibly tired because he had to get up so early to be able to catch a connecting flight to get here. 

Y/N hugs her little brother around his waist and rests her head on his chest to hear his heartbeat. He’s not little anymore but he’s still little to her, “I’m sorry about all of this, Jack,”

Jack rubs her back and wraps his arms around her, “Don’t worry about it, and hey, I get to be in Jamaica, not bad, eh?”

They chuckle. It’s a great reunion. If only the circumstances were different.

After the initial greetings, they sit down on their balcony. Dean had someone bring in drinks and snacks. Sam’s still on the phone and Ruby is inside, changing into her bikini. 

Jack sits next to her and she can feel that he’s a little restless as he can’t hold still. 

Dean notices it too, while he pours water into glasses and raises an eyebrow at Jack, “You okay there, Jack?”

Jack’s blushing, “Yeah,”

He usually never blushes but now he does and she doesn’t know what it is, but she thinks it’s cute.

“Do you wanna take a dip in the sea?” Dean asks and grins. 

“Can I?” Jack’s face lights up when he hears that Dean basically just read his mind. 

Dean shrugs, “I saw you eyeing that blue water, so yeah, knock yourselves out. We’ll start when you’re done.”

That’s pure Mr. Winchester. She thinks it’s a gift that Dean has because he can read people very well. Maybe that’s the reason why he’s so successful.

“Awesome!” Jack stands up and gets rid of his shirt, he was so excited that he boarded the plane in his swimming trunks, bless his heart, “I’ll be right back!”

“Hey, be careful!” Y/N shouts after him but Jack’s already taking a dive.

Dean sits next to her when Jack’s down below, splashing around in the sea, “I like him,”

“He doesn’t like you,” She grins and moves closer to Dean, hooking both her legs over his lap and he strokes her thighs and leans back into the seat. 

“I know that,” He says, and she leans back too, places her head on his shoulder. Dean pecks the crown of her head. It’s become so natural for him so show her little affection. Little does he know that it means way more to her than it does to him, “I’ll get him to like me, you just watch.” With another breath he adds, “You know, you two remind me of me and Sam. Just that Sammy is a bigger pain in my ass.”

  
  
  


*

  
  


After another attempt of gathering everyone together, they finally sit down to talk. 

“How did Amara know that we’re here?” Y/N voices her thoughts. 

“Uh,” Ruby says, “That might have been my fault. Remember her walking in on Friday?”

Yeah, how could she forget that. She was under the fucking desk blowing her fucking boss. 

“Anyway,” Ruby continues, “I had the screen open for your holiday resort and since she had to walk past my desk in order to get to Dean’s office, I’m sure that she saw it.”

“It doesn’t really matter, actually,” Dean says, “She’s here, there’s nothing we can do about it.” He clears his throat before he goes on, “I’ve spoken to Ash and I asked him to find out things about Arthur Ketch. Turns out, he’s not a descendant of English aristocracy but a private investigator. It took Ash the whole night to find that out because there’s not much info on the guy.”

“What?” There are a couple of voices throwing that in.

“Means, that he’s here because she paid him to spy on Y/N and me. Probably get some footage of us not being married so she can expose us.” Dean says in a low voice. 

“Would someone please explain what is going on?” Jack throws in. He's right. They still didn’t explain their situation to him. 

“We’ll get there, Jack,” Dean says, his voice is softer, “I’ll get back to you, alright? Just have a little patience.”

Jack purses his lips into a thin line and leans back in his chair. 

“Do you think they’re still here?” Sam asks, “We didn’t see her when we walked through the resort.”

Dean scoffs, “Sammy, it’s Amara, what do you expect? Of course she’s still here. She’s like the black fucking plague, she won’t go away easily,” he sighs, “All I know is that she’s here and we’re being spied on, so since you are all involved, I want you to get your story straight and don’t let anything slip that would jeopardize this, you understand?”

Everyone nods, except for Jack and Dean notices that, too. He walks over to Jack, places a hand on her brother’s shoulder, “I need to talk to Sam for a bit and after that, I’ll be right with you, okay?”

“Yeah,” Jack snorts, “Sure,”

She can see that Dean is feeling Jack’s rejection, but instead of arguing or explaining more, he gives Jack space. Dean nods his head and walks inside with Sam, leaving them outside. 

  
  


*

  
  


Y/N and Ruby are floating on swimming mats in the sea below their bungalow while Dean has taken Jack on a deep sea fishing trip to explain it to him. She wanted to go too, but Dean said that it’s something between him and Jack, since he’s the one who put Jack in this situation in the first place.

Jack was quick to agree, because her brother loves fishing. Their dad used to take them finishing a lot while he was still alive. She wonders how Dean knows because Ruby doesn’t know these little details. She’s known Ruby since she started to work for Dean and she’s become her best friend since. Ruby knows a lot about her, knows about her past relationships, but Ruby doesn’t know a lot about her relationship with her brother. Y/N never thought it was relevant to their friendship. All she let Ruby know was that Jack was the most important person in her life.

So the two of them left right after Dean discussed things with Sam and they would be back in the evening. Sam’s somewhere, trying to spot Amara and maybe scare her a little with some lawyer lingo. She doesn’t really know. Fact is, that there’s not a lot that they can do because technically, Amara’s allowed to be here. She wonders why Sam and Ruby came at all, because they aren’t necessarily needed, but as Dean said, Sam saw the opportunity and Ruby’s not going to say no to a couple days of fun in the sun. 

“So, how’s things with Sam?” she asks Ruby, because since they arrived all they’ve been talking about is Dean and Y/N’s fake fucking marriage and she can’t listen to that anymore. 

Ruby smirks, “It’s good. He took me on a trip to Jamaica.”

Y/N snorts, “Yeah, I can see that. On Dean’s expense, apparently. That cheeky little bastard.”

“I like him, Y/N, he’s the best lover.” Ruby gushes, “I can honestly see us being more than just  _ this _ , you know? Maybe it’s the beginning of something good?” 

“Won’t it be weird when you work for the same company?” It’s a legitimate question. 

Although the company’s contract doesn’t have a clause that says that they aren’t allowed to strike up a romantic relationship at the workplace. Still, she can imagine that Dean probably wants to make sure that people stay professional while working. Which is really a little hypocritical of him, given what they’ve already done in his office.

“Well, is it weird for you?” Ruby raises an eyebrow.

Y/N swallows, “We’re not— It’s not—” 

Her friend scoffs, “Yeah, sure, you keep telling yourself that.”

“My god, Ruby, it’s really—,” She sighs, “Okay, we get along, alright? But we’re not like,  _ anything _ , I think? At the end of the day, it’s just business.”

“Who are you trying to fool?” Ruby laughs. 

“What do you mean?” 

“Y/N, for God’s sake, wake up!” Ruby squirts water in her direction, “I think everyone knows but you, and that’s pretty frustrating.”

“Know what?” She squirts water back at her friend to conceal the red flush to her face. 

Ruby sighs, “How he behaves around you? He always makes sure that you’re okay. Every fucking day he would come by and ask if you’re alright? It was like that since you started in the office. Have you not noticed?” She opens her mouth to protest but Ruby goes on, “And don’t give me that ‘ _ But he’s asking you too’ _ . What do you expect? He’s standing right there in front of us. He can’t be asking you without asking me too.”

“Ruby, that’s absolute bull,”

Her friend snorts, “I started to work there six months before you came along. He did not stop by and ask me once if I’m okay before you got there, Y/N. I never told you that, but I’m telling you now, it’s not his normal behaviour. He cares, and that’s just that. Take it or leave it. But maybe you’re so traumatized by Kevin, that you don’t really know what’s good if it hits you square in your face.”

“It’s just for show,” She mumbles, not entirely sure of her own words either. 

“Why do you think Jack’s so hostile towards Dean, huh?” Ruby scoops sea water and drips it over herself to cool down, “I’ve met Jack several times, and think I know him a little, Y/N.”

“Oh, come on, leave Jack out of this,” 

Ruby raises an eyebrow, “I won’t. Because you know why? Jack’s overprotective of you. He’s your little brother, he thinks that he has to look out for you. The only way he is like he is with Dean, is because he sees through him. Jack knows and that’s why he’s going to give Dean a hard time because he doesn’t want Dean to break your heart.”

Y/N sighs, “Ruby, it’s really just for show,”

“If you say so,” Ruby shrugs and chuckles to herself. 

Ugh, she hates that. Is she really the only one who doesn’t know shit around here?

  
  
  


*

  
  
  


They’re waiting for Dean and Jack at the restaurant. Dean had called to say that they’ll be in a little later and that they should go ahead and he and Jack would catch up. 

So far, there’s no sight of Amara yet. Sam hadn’t found her either. Could it be that they have already left or maybe they’re just really good at hiding in fucking bushes around here. She wouldn’t be surprised if they bugged everything just to hear one of them slip.

They have ordered drinks and were chatting away when Dean and Jack arrive, both freshly showered. Jack already has a little tan from fishing. He looks good. He looks genuinely happy and it’s a drastic change from the Jack that arrived here this morning. 

The chair beside her is empty as well as the chair across from the empty chair, and she sees that both of the men were aiming for the one beside her and Jack got there first, but then Jack quickly changes his mind to let Dean sit next to her. 

Dean takes a seat and leans in to kiss her cheek. She catches a whiff of his cologne and takes a deeper breath because it smells so good. By this stage, they have perfected their lovey dovey couple routine like Sam suggested on the first day, and Sam grins when he sees how natural they’re handling it. 

When she looks up, Jack’s winks before he grins brightly. 

She leans into Dean to whisper in his ears, “Who is that and what have you done to my brother?”

Dean has to chuckle at that, “We talked, everything’s fine.”

“No, seriously, what have you done? You exchanged him with a robot, didn’t you?”

He tilts his head towards her. Their noses almost touch, his hand comes up to cup her chin and he kisses her, smirks after he parts, “Baby, it’s okay. We talked it out. We’re good,”

She doesn’t quite trust Dean. Something doesn’t sit right with her but she doesn’t say anything. She’s got to find a time to talk to Jack in private but maybe not here because she never knows who could listen into them. She’ll have to do it as soon as they’re back home.

After the meal when they are waiting for dessert, Dean looks over to Jack, “You wanna tell them or shall I?”

“Tell us what?” Y/N frowns, already thinking of the worst. Thinking about Jack telling her that he drops out of college or some shit.

Jack grins, “Nothing bad, Y/N. Dean offered me an undergraduate work experience at his company.”

“Yeah, he’s gonna be looking into the company for three months, if he wants he can stay longer.” Dean says.

“And what did you say?” She asks her brother.

“Of course I said yes,” Jack’s smile widens, “That’s going to look awesome on my CV.”

She can’t find it in her heart to object. Not when her brother’s smile is so big.

  
  
  


*

  
  
  


The others went on to the bar but she decided to call it a day. She parts with her brother, telling him to behave or else Sam’s gonna beat his ass. Jack didn’t find it very funny, though. Dean insisted on going to the room with her, although she said that he doesn’t have to.

Back in their bungalow, they strip to their underwear and brush their teeth. She takes her time to wash her face and when she walks out, Dean’s already laying in bed. The AC needs some time to catch up and it’s too warm to pull the cover up. 

Y/N slides into bed next to him, curls up to his side and Dean abandons his phone to wrap an arm around her. 

Dean kisses the top of her head, “You okay?” His fingers of the hand around her strokes at her chest, goes down to her boob to pinch at her nipple. She yelps out a laugh and he laughs with her. 

“Yeah,” She says, turning in Dean's grip to lay her cheek on his chest, “Thanks for talking to Jack. Although I’d like to know what you talked about.”

“If I’d tell you that, I’d have to kill you.”

“Of course,” She groans, and changes the subject because she’s not sure if she wants to know. She’s not entirely sure if the things that he’ll tell her won’t break her heart and for the time being while they’re still in paradise, she’d rather keep up the facade and continue to enjoy what they have, “You sure about the work experience thing for Jack?”

“I’m pretty positive. He’s a bright guy. I think he’ll be a great addition to the company.”

“And you’re not just saying it because you owe him.”

Dean breathes out a weak chuckle, “Well, that I do, too. But no, we got to talk about his studies and I trust my guts. I’ve never been wrong.”

She tilts her head up to raise her eyebrow at him.

“Hey, two or three people this year, it’s not much.” He’s talking about the people he fired. 

“Twelve, Dean.”

“Yeah, well, but I did not interview any of them, so it’s not my fault my people don’t have good people reading skills.”

“Oh and you do?” 

“I do.” He says, without even thinking. He’s so full of himself, it blows her mind. 

“But I don’t know where Jack should stay for the whole summer. Like, my apartment is barely big enough for myself.” She’s only voicing her doubts. She’s sure that they would manage. Maybe she can go live with Ruby for a while. 

Dean’s quick to jump in, “He can live with me,” 

“What?”

“You heard me,” Dean chuckles, “I have plenty of space and maybe you can drop by every now and then,”

He’s really talking about life after the court date, isn’t he? Talks about her going back to her old life and they resume what they are not and occasionally going to social events together as a fake married couple. She really doesn’t want to think about it yet. 

So, instead of spilling him all her doubts, she says, “Yeah, why not,”

Smiling, he pulls her on top of him and one of his hands goes around her waist while one of them tucks a strand of hair behind her ear as he kisses her. She likes that, likes his kisses. They make her forget everything around her. The touch of his tongue electrifies her. It makes her feel something tingling down there and she clenches around nothing. 

Yes, it’s good, she decides. She’s going to enjoy the last couple of days. She’s going to take what she wants, fill her heart with only happy memories so she can take them out and relieve them whenever she feels down. Maybe if someone treats her bad, she’ll think back and know that there’s someone out there who could treat her like Dean does.

She kisses along Dean’s jawline, down his throat and he cranes his neck, giving her better access. His scruff feels rough on her tongue. Sucking down a path, she kisses his chest, licks at a couple of freckles and it’s tickling him because he’s chuckling. She works her way to his nipple and Dean moans a little when she sucks and tickles them with the tip of her tongue. Grinning, she works down his body, dips her tongue into his navel before she kisses down his happy trail until she’s slotted between his thighs. 

Looking up at Dean, she sees him looking at her with hungry eyes, that are a shade darker than usual. She grins as she lowers her face and places a kiss on his hardened cock through his underwear. She licks a broad stripe across the fabric along his shaft, and he bites down his bottom lip, swallowing down a groan that wants to leave his mouth.

Hooking her fingers into the elastic of his underwear, she slowly pulls the fabric down. His hard cock springs up and hits her nose. She has to giggle and Dean’s biting back his laugh. 

She sits up a little to get the underwear off his legs and slots herself back on her elbow in between his thigh, stays on her knees and sticks her ass out for the visual effect. Dean opens up so easily for her. 

His dick is hard, and leaking a little at the tip, but she takes her time, her hands are on his thigh as she opens them up a little further. She plants little kisses on either side of his thigh, close to his balls and he groans some more.

“Tease,” She hears him say and chuckles at that. 

Finally she plants a kiss on his sac, and begins to lick and suck him there. She still doesn’t touch his dick but she feels it twitching and it feels heavy on her nose and forehead. Her tongue works around one ball, sucks it in to release it with a lewd pop and then she goes further down, licks on the underside of his sac, and Dean opens up his legs some more, giving her better access. 

She’s learned that trick from Ruby. She said men would not admit it but a whole lot of them like it. She always wondered if Dean does, and apparently, the answer’s  _ yes _ . 

Her hands lift up his legs, and he spreads them even more as she toys her tongue along his rim. 

“Jesus fuck—” 

Chuckling, she licks some more, his balls are resting on her nose. God, he tastes even good there.

Dean’s breathing hard above her and she moves further up again, taking his leaking tip into her mouth and starts to bob her head. She can’t take him to the hilt, but she really tries, gagging around his dick as tears start to pool in her eyes. 

After a while she changes into normal sucking, works the hard lengths in her hand while she toys at the tip of his dick, paying attention to the sensitive string. 

“Just like that,” He whispers low and deep, “Good girl, looking so good with my cock in your mouth, baby.” 

At these words, she bobs her head a little faster, sucks a little harder and Dean has to pull her off abruptly, “Woah, not so fast,” He chuckles with a shudder, “Don’t wanna blow too soon.”

He pulls her up by her arm, kisses her roughly, all sloppy wet and he groans as he sucks his own taste off her tongue, “Come on, ride my face,” His fingers are already tearing at her panties, pulling them down and she stands up to step out of them. She kneels down and his hands quickly finds her pussy, threads his fingers through her folds and unceremoniously plunges two of his thick fingers inside, making her moan out loud while he latches at her tit to suck and bite at her nipple. Her hands find his head, fingers digging into his scalp. 

“God, I want you inside,” She moans as his mouth licks a wet trail to her other nipple. 

“I have to taste you first,” He groans with her nipple in his mouth, “Just a couple of licks, please? Fucking love how you taste,”

She’s awfully wet but she just got wetter hearing his words. 

What is this man doing to her?

Dean lets the nipple out of his mouth with a smacking sound, and he breathes hard as he slides down the bed a little and maneuvers her on top of him. 

Fuck, his mouth seals around her clit and he starts to lap at the juice around her cunt. His hands are on her boobs, kneading them and tweaking her nipples. It feels so good and she can’t help but grind down into his face. Dean doesn’t seem to mind because he’s humming. It sounds as if she’s the most delicious thing he’s ever eaten and the sound of it turns her on.

Y/N’s so close to coming but she can’t possibly come on his face, can she? She’ll make him all messy and—  _ oh god _ , there’s no stopping the pleasure wave that rolls through her legs up to her cunt. She’s coming strong and hard, pushes her pussy down into Dean’s face and she’s almost falling off him if it wasn’t for his hands on her tits keeping her upright.

She climbs off him, sits square on his chest with her pussy still tingling and Dean laughs, his face shiny from her cum. 

His smile is cocky, all bravado and boyish youth, “Told ya it wouldn’t take long,”

She rolls her eyes and he slaps on her ass, “Come on, ride me,” 

Dean helps her move down because she doesn’t know if she can on her own with her body still trembling. But when she regains her composure, she lays his twitching dick down and spreads her wet pussy lips around it, grinding on his shaft. It gives her the right friction but apparently, he thinks she’s a  _ goddamn tease _ .

Y/N gives in, slips his dick inside and sits down slowly, letting him stretch her wide and he groans at the squeeze. She’s always so much tighter after she comes and it would take her a little while for the cramping of her walls to go away.

Bracing her hands on his chest, she starts to ride him, and he helps her with his hands around her hips. She switches into grinding after a while and has to moan out loud at how deep he’s inside. 

“You looks so good,” Dean’s hand works up her stomach, cups at her tits and twirls at her nipple, making her arch her back, “Fucking perfect,” 

She feels her orgasm approaching again, because her clit rubs perfectly against his pelvis and his huge dick is in her fucking cunt, oh my god, she fucks him faster. She comes with a loud moan, pressing her legs together and Dean squeezes his eyes shut at the pressure, he pulls her down by her arms, crashing her lips to his as he grunts out into her mouth and he buckles his pelvis up, his dick throbs and twitches in her cunt. 

“Fuck,” He breathes out against her mouth, kisses her there, and pecks her nose, “Fuck,” He repeats and he smiles at her. 

  
  
  


*

  
  


They take another shower before they settle back into bed and Dean has already turned off the lights when his phone rings. 

He takes it to look at the screen, “Chuck,” 

  
  



	18. CH18

Y/N’s getting dressed as everyone is meeting in their bungalow, as Dean received big fucking news.

News that could mean that this will all be over sooner than she thought it would be.

She’s not sure if she should be happy or sad about it. Maybe both. Happy that they finally have proof that Amara played a stupid fucking game. Sad that their arrangement will eventually come to an end. Does she regret it, though? No, she definitely doesn’t. It was a decision she made and she owes everything that comes with it. 

  
  
  


*

  
  


The others were still at the bar when Dean called Sam and so everyone is coming with him. She just hopes that they are still sober enough to process the news.

Sam’s the first to come in and he starts to laugh, “Dude, it stinks of sex in here!”

Ruby giggles behind him. 

Dean and Y/N both look at each other before they lower their heads. Sam’s not wrong and it is actually kind of embarrassing.

Jack is the last to come in, and if he heard Sam’s remark, he pretends he hasn’t. He closes the door behind him, while the others make themselves comfortable on the couch. 

Y/N stands behind the couch and Jack comes to stand beside her. Dean’s paces around the room. The laptop is propped up on the little coffee table.

“Chuck called,” Dean says when they all have settled, “Look at this,” He hits play on his laptop and they all have their eyes trained on it. She looks too, even if she’s seen it three times already.

It’s security footage of Dean’s night in Vegas. The night he married Amara.

They can see Dean, Chuck and Amara sitting around a table. A waitress in a skimpy outfit approaches with their drinks and sets it down. While the waitress sashays away, both men stare at her ass and that’s when Amara drops something into Dean’s drink.

“Yeah, alright, that was inappropriate,” Dean says and looks into the round before his eyes settle on Y/N, “Definitely never gonna do that again.”

She shrugs. It’s not like he has to explain himself. And especially not to her.

“So she really did drug you!” Sam grins wide and bright, “We have fucking proof!” He stands up and hugs his brother, “Does Amara know it exists?”

“Of course she doesn’t, Sammy!”

“Good, we keep it between us,”

“What does that mean now? Can you do something with it?” Dean asks.

“Duh! That’s good because it means that you don’t have to pretend anymore. As soon as the Amara case is over, you and Y/N can stop being married. We will make sure your marriage is annulled in a timely manner.” Sam says, and adds, “Or… we can go forward and sue Amara’s ass right away. If we’re lucky, we can get a court date sooner than the one we already have. Or we can just hold on to the tape and still wait for the annulment hearing and show it to the judge, and we can still sue her later.” Sam shrugs, “You decide.”

Dean gnaws on his bottom lip, “Yeah, I need some time to think.”

“Sure,” Sam says and pats Dean’s shoulder.

  
  
  


***

  
  
  


She wakes with Dean spooning her from behind, his arms tight around her, his nose nuzzles against the back of her neck. He’s awake. She knows, because his heart’s beating faster than it would if he would still be sleeping. She has got Dean’s heart rate down to the tee by now.

“Did you sleep at all?” She whispers and lays her hand on his arm that’s around her. She strokes up and down and he holds her just a little tighter.

“Not much,” Dean mumbles, warm air hits the back of her neck. 

“Have you decided?” 

“I have,” He says, “We’ll wait til the hearing. It’s going to be in two weeks.” He kisses her skin, leaves his lips there and mumbles, “We still got two weeks.”

“Okay,”

Dean places another kiss on her bare shoulder, “You mind if we go home on Saturday?” 

That would mean three days earlier than they were supposed to be leaving.

“No,” She says, “No, I don’t,”

“It’s just, I want to meet with Chuck and listen to his strategy and get Sam to get working on building a case. I want to be ready,”

“Dean, you don’t have to explain. It’s okay,” She turns around in his grip and he props himself up on one elbow to look at her.

“You sure?”

“Yeah,” She smiles, “Seven days in Jamaica is more than I could have ever asked for. We still have two days left, so it’s really no problem.”

Dean replicates her smile, “Good, we all fly home together. You can see your brother off,”

“Okay,”

He kisses her cheek, the corner of her mouth, hovers his lips there, “And we’ll go for dinner at my parents on Saturday evening,”

“Oh—” 

Before she could say  _ no _ , Dean kisses her, bruisingly hard because he knows that she doesn’t want to do that and he chuckles into the kiss. The little shit.

  
  
  


***

  
  


The next few days went by fast. They went on a hike, and swam with dolphins. They did anything to get away from the resort to avoid Amara. 

On their last night, they went out for a meal together. Everyone is tanned and happy, and she really likes it. Likes the sparkle in their eyes, likes the easiness of their group. Likes how they can make each other laugh. It’s easy with them and she wishes sometimes that Dean wasn’t her boss. He’d be a great friend. They’d all be a great group of friends, actually.

They were all going to go to the bar after the dinner and this time she agreed because it’s their last night, even though she still hasn’t packed. After the first drink, she notices Dean has been silent for a long time. As if there’s something that bothers him deep within. She can’t really read him and that is really frustrating.

He’s sitting on a bar stool and she’s standing just in front so she turns around, cradles his face in her palms. He hasn’t shaved, his scruff’s a little longer than it usually is.

Y/N places her forehead to his and feels his hot breath on her face, “You okay?”

He smirks, but it looks a little strained, “Yeah,”

She doesn’t believe him, but she kisses him, teases her tongue along his bottom lips. Dean kisses her back, slides his tongue next to hers, his one hand grips around her waist, fingers digging deep into her flesh while he holds her tight, as if he doesn’t want to let her go. 

“I want you so bad,” Dean’s breathing hard when they break their kiss for air, “Let’s go,” He whispers, kisses her once more.

She licks her lips, bites down on it, and nods at him, “Okay,”

Standing up from his bar stool, he takes her hand in his, and calls into the round, “We’ll see you tomorrow guys,”

They didn’t really pay them much attention. Jack’s talking with Sam while Ruby’s dancing on the dance floor. 

He drags her along the pier, and she has to run to keep up, “Dean, not so fast!”

“Oh, I’m sorry Miss short legs,” He chuckles and gets even faster instead of slowing down. 

As soon as they’re inside, he has her pinned against the door, kisses her hard and needy and his hands are around her thighs, lifting her up to carry her to the bed. 

Dean drops her off and helps her out of her dress, all the while still kissing her. He kneels over her, his hands cups around her breasts, thumbs over both of her nipples. He drags his tongue along her throat down to them, sucks in a nipple one by one before he goes further down. His fingers hooking into her panties, taking them off her legs and then he gets off her and the bed completely before pulling her to the edge of the bed by her legs. 

He kneels down on the floor, his hands on her knees as he spreads her. His eyes stare between her open legs for a while before he sticks out his tongue and licks across her clit. She arches her back at the sensation, her hand finds his head. 

His fingers join his mouth, sliding two of them into her wet cunt as he continues to suck at her clit. 

“Fuck—” She moans, her nails scratching at his scalp.

His fingers are curving up on the inside. They rub against her sensitive spot and she squirms below him because he sucks and hums at her nub. 

“Oh my god, right there. Don’t stop, don’t stop,” She’s panting hard, her toes start to curl and then she has to close her eyes because of the pressure, “Fuck!” Her legs cramp up and she digs her nails deep into his head as she comes so hard she sees fucking stars.

Dean doesn’t stop to lick until her convulsions stop. She shudders all over and only then does he let go of her as he takes a step back to take off his shirt and pants, drags them down together with his underwear. 

Y/N props herself on her elbows to look at him, and has to bite down on her bottom lips when she sees his hard cock, the top slightly pink. 

He licks his hand and starts to jerk himself off when he walks closer, bending down to kiss her and his face is all wet from her cum. 

“Move up the bed,” He whispers and she does, goes further up and lays her head on the pillow. Dean follows her, walks on his knees to where she's waiting. 

Dean gets between her thighs and she spreads her legs for him. His one hand holding her open by her knee while his other hand’s holding his dick. He drags the head along her wetness, slicks it up before he pushes in slowly. Almost agonizing slow.

Before he bottoms out, he lays down, his one arm around her shoulder while the other one strokes along her thigh. He kisses her, sloppy and lazily, while he moves inside, goes in deep and slow. It’s different to the other times they fucked. It’s less rough, less raw. This is soft and gentle, it’s need, and heat, and want. 

He kisses down her jaw, sucks at her pulse point, “So good,” He breathes against her skin, “You feel so good around me, baby,”

Y/N claws at his back as he claims her mouth again, kissing her deep, making her gasp into his mouth when she comes from his cock alone. He sucks in her tongue, bites on her bottom lip, grunts against her mouth when his body trembles with his release. 

They stay connected, their bodies melt against each other while Dean still sprays kisses at all the places he can reach in this position. 

After a while he lays his head on her shoulder, sucks in her skin. Dean pulls out gently to be able to lay his head on her chest and she strokes his head. She knows that he listens to her heartbeat. 

His one hand lazily rubs at her sensitive clit and she jerks a little, feels his cum running out of her. He catches it with his fingers and brings it up to her mouth and she willingly opens her mouth to suck at them. He groans as he watches her suck his fingers clean, “You’re definitely something else,” He chuckles and kisses her again.

“Ugh, we still need to pack,” She whispers after a while of lying tangled together. 

Dean lifts his head off her chest a little, “Just a little longer, okay?”

She kisses the top of his head, “Okay,”

  
  
  


*

  
  


They manage to drag themselves up to go brush their teeth and wash their faces. But packing would have been too much to ask for, so they end up setting their alarm an hour earlier than they needed to be up and crawl right back into bed. 

Dean opens up his arms for her and she crawls in, lets him wrap his strong arms around her, let him kiss her forehead and stroke her back.

It feels right and she’s more than sad that this will be all over in two weeks time. But she can also count herself lucky because in these two weeks, she has felt more love than other people have in their lifetime. 

  
  
  


*

  
  
  


She wakes in the middle of the night to Dean raining kisses all over her face. When he feels her stirring awake, he cups her chin and tilts her head up to kiss her properly. 

His dick is hard. It stands out and pokes at her stomach and she takes it into her hand, jerks him slowly, making him groan into her mouth. 

“Turn around,” He whispers, nibbles on her bottom lip.

Y/N does, turns around in his grip and Dean sprays kisses along her neck and shoulder. She feels the blunt head of his cock threading through her folds. It’s gotten wet again and it’s still filled with his cum from before. He slips in easily but instead of going in deep, his movements are slow and shallow. 

Dean fucks her softly, his mouth latching onto her skin. It’s only about three thrusts of his hips later that he grunts into the base of her neck, lips ghosting over her skin. 

He chuckles, drags his teeth along her flesh, “That was unexpected,” He places another kiss on her shoulder, “‘M sorry,”

She has to grin, but she doesn’t say anything.

They stay connected, Dean’s not pulling out, nor does he move away. Instead, he presses himself closer, holds her tight and she doesn’t know how long it takes but she eventually finds sleep. 

  
  



	19. CH19

The alarm pulls her right out of her sleep but Dean’s already awake. He doesn’t move though.

“I don’t wanna go home,” She mumbles, rubbing at her eyes. 

“Me neither,” Dean whispers, “But this is actually the third time the alarm has gone off, so we should maybe get going and pack,”

Her eyes fly open in horror, “Dean!”

“What?” He’s chuckling, kisses her neck, “You looked so peaceful, I couldn’t bring myself to wake you up.”

She rolls away and out of bed while Dean tries to grab her but his hands clutch around emptiness. 

They pack in record time and Dean joins her in the shower after. It’s hard to just shower and not do other things like they usually do. It’s hard to not just let him fuck her. 

  
  
  


*

  
  


They’re on the plane home, and she sits next to Dean. There aren’t many people on the plane and especially not in the first class. Jack’s sitting on his own in the seat across from Y/N and Dean and he has his earphones in his ears. 

After taking off, and after she let Dean help her over her anxiety of flying, she looks over to see how Jack’s doing, sees him looking out of the window as the plane leaves the island.

Dean’s typing away at his phone but he notices her, “Go on, you gotta spend time with him,”

“Yeah,” She smiles and stands up to walk over. 

Jack takes his earphones out when he feels her presence. He opens his arms for her to loop her head through, “Hey,”

“I remember you always loved flying,” She smiles. 

Jack grins, his lips curve up wide, “It’s awesome!”

Y/N has to chuckle at his enthusiasm, “Don’t get used to it, though.” With the next breath, she adds, “I’m sorry things turned out the way they did. I just thought about you and your education.” 

Jack tilts his head to look at her, “It’s okay, Dean’s not bad, you know,”

She looks over to where Dean’s sitting. He’s still typing something into his phone. With a smile, she says, “No, he’s not,”

  
  
  


*

  
  
  


When they land, they have to say goodbye to Jack because he has to take a connecting flight. She doesn’t really want to let her brother go and clings on to him, her arms wrap around his middle, while Jack rubs her back.

“I’ll see you soon, alright?” She says, “I’ll come visit,”

“Sure,” Jack places a kiss on the crown of her head, “We’ll see each other again in the Summer,”

Y/N looks up to her brother with a smirk on her face. She’s trying her hardest not to cry, “What did you and Dean talk about?”

There’s a grin on Jack’s face when he lowers himself to her level, “If I tell you, I’d have to kill you,”

She rolls her eyes at that and Jack laughs. 

  
  
  
  


*

  
  
  


After they reach Dean’s apartment, Dean goes out to meet with Chuck and Sam. She’s left to unpack and relax but that’s perfectly okay, because she wants to mentally prepare herself for dinner with his parents later. 

Y/N really, absolutely, doesn't want to go but she’s still his wife for two weeks. She had asked Dean why he didn’t tell his parents the truth and he just grinned at her, telling her that she didn’t need to worry. That he’ll tell them the truth, that he’ll come clean. That’s the whole purpose of them going there. Because he wants them off his back. They’ve been calling every day apparently, and he just wants them to stop pestering him when he has other things on his mind.

Late afternoon, Dean’s back, and he looks happy. She doesn’t ask, doesn’t really need to know. She’s doing what she agrees to do and the rest is in the hands of Dean and his team. 

He takes a shower and she’s finishing her look. Not that there’s too much to finish. She wears the same dress she already wore to the restaurant when they went to meet Chuck. It’s really her best dress, something that parents would probably approve of in their daughter in law. She doubts that Dean’s parents will, but other parents would for sure.

Y/N’s waiting in the living space when Dean walks out of his room, he looks good, wearing trousers and a white shirt, sleeves rolled up, top two button loose. The white of his shirt brings out his tan. She can see the freckles, even when it’s darker. It’s a casual look, a mixture between his holiday look and his business look, and he smells heavenly. 

He smiles when he walks closer and weaves an arm around her waist to pull her close, “You look beautiful with that holiday glow,”

She has to smirk when he places a kiss on her cheek, “You look great yourself, Mr. Winchester,”

There are tan lines around his crinkles.

“You ready?” He asks and pushes her towards the door, his hand on her lower back. 

“‘M not.”

“Yeah,” He huffs out a breath, “Me neither,”

  
  
  
  


*

  
  
  


Dean’s parents live in a big villa with a huge driveway. There’s a light up fountain in the middle. It looks like one of the houses she has only seen in movies. 

“Wow,” She says in awe. 

Rich people really know how to live, don’t they? She can’t even imagine what it’s like to live here, to have grown up here. She can’t imagine what it’s like to have a butler ready to open the door for her. Can’t fathom having chefs and maids, having a driver and personal trainer. 

“You grew up here?” She asks him as they step out.

“No,” Dean says, “You’re an employee. You should know about the history of the company and how I got where I am now, no?”

“Ugh, I should, shouldn’t I?” She grimaces and Dean’s full on laughing. 

“Dad started from scratch and he made it grow and successful, although I made it grow even more and it’s more successful and bigger than it was under my dad’s wings.” Dean’s hands are on her waist as he leads her up the steps to the front door, “I didn’t exactly grow up poor, Y/N, but we weren’t rich either. Dad only bought this property two years ago. The home I grew up in is much, much smaller.”

“Is there something I need to know before I meet them? Something I shouldn’t say?” 

Dean stops, places his hand on her shoulder to turn her towards him. He pretends to think and after a while he says, “No, you just be you, okay? I would never ask you to change to impress them. Let me speak. Only speak when you’re spoken to. That way we can avoid any unpleasant questions they might throw at you.”

“Okay,” She says, and suddenly her heart pumps faster. She’s nervous as hell.

He smiles a little, cups her chin between his thumb and forefinger, “You’ll be fine, I got you,” He pecks her lips, lingers there a little longer than necessary. 

Although she wants to stay like this, she knows that Dean eventually has to pull himself away, eventually has to ring that damn door and she eventually has to face her fake fucking in-laws. 

A maid opens and they step into a big hall. Everything looks so neat and flawless. It’s all white and beige marble, and she feels the urge to take off her shoes because she doesn’t want to ruin the floor. 

“There you are!” A woman walks in, tall, blonde, a smile wide on her face. She assumes that it’s Dean’s mother. The woman’s dress is so nice, it puts her nicest dress to shame. 

The woman comes closer and Dean leans in to peck her cheek, then he straightens himself, “Y/N, this is my mother, Mary.”

Mary takes her hand in both of hers, clutches at them tightly, “I’m so happy to finally meet you, Y/N.”

“It’s nice meeting you, too, Mary. Thank you for having us over.”

“Ah, it’s no big deal. We were dying to meet you! Come on, John’s already waiting at the table, he’s hangry,” Mary chuckles and places her hand around Y/N shoulders to walk her into the dining room. Dean sighs and trails behind. 

Dean’s father stands up from his chair when he sees them walking in, and he smiles. It’s bright and wide, almost the same smile as Dean’s. She can see that he certainly got his boyish charms from his father.

John places both of his arms on her shoulder and leans in to peck her cheek immediately, “Hello, Y/N, it’s nice to meet you.”

She nods, repeating the same line she already said to Mary and they sit down right away. Apparently his parents don’t mess around. Maybe they want to get it over with as much as she does? 

The first question comes during the appetizer, “How did you meet? At the workplace or did you know each other before?” The question came from Mary and although she looks at Y/N, she didn’t address her directly, so Dean takes a napkin and brushes at his lips before he swallows and speaks.

“Y/N used to work in the coffee shop close to the office building and she regularly delivers coffee for other offices there. I walked out one day to grab lunch and she bumped into me. I could have saved her from falling, but the collision spilled the coffee, wetted my suit too.”

She squints at the memory. It was all her fault. She wasn’t looking at that time. Dean was so pissed and she was afraid that he would lash out and rip her a new one right there in the street, but he didn’t. He was dressed so nice that day and she had to go and pour coffee all over him, ruining his suit and probably his day.

Dean is looking over to her with a small smile on his face, “And I went in there about a week later. She thought I was there to talk to her manager, but I just wanted to see if her ankle was fine because I remember her limping a little afterwards. I watched her work and saw how she reacted under pressure, saw how she behaved around her colleagues and customers and that’s when I thought that I wanted to offer her the job as one of my assistants. Ruby needed help and she already knew Ruby because Ruby was in that coffee shop quite often. She said no. But I went in every day until she said yes.” He leans in to press a kiss to her cheek. It makes her face flare up. Partly from the kiss but also from the way he remembered details.

It’s true, though. Y/N remembered him telling her about a job that would be perfect for her. That she could earn much more by working for him. She had consulted with Ruby about it and after weeks of Ruby telling her that the company was really good, she finally agreed to the job offer.

“That’s a lovely story,” Mary says, “Does she have the required degree though?”

Well, Mary, she does not, but thanks for asking. 

Y/N never attended college having to take jobs to hold her and Jack above water.

“Mom, a degree is just that, a degree. It doesn’t say anything about your work ethics, your integrity or willingness to work a job. I don’t think most of the people I employ have made it through college. It’s about what they are capable of. She’s smart and she’s doing a fabulous job.” Dean’s voice rolls deep. She can feel that he’s trying to keep himself together. 

The maid came to take their empty plates. Hers is not empty but her appetite is gone. 

“Still, it tells me that she’s not actually qualified to do her job. And qualifications are important.” John chimes in with a somewhat unnecessary addition.

“Do you have a prenup?” Mary asks.

Wow, Dean’s mom goes straight to the point. She wonders how long Mary’s been holding it back. But hey, Mary made it past appetizer.

“Mom!” Dean gets a little louder.

“Relax, Dean, I was just asking,” Mary tries to sound nonchalant but adds with her next breath, “Do you?”

Y/N folds her napkin and places it neatly on the table before she stands up, “Excuse me, where’s the powder room?”

“Tessa can show you,” Mary says, a fake small smile on her face, and then she calls out for the maid, “Tessa, can you please show Y/N the way?”

“Sure, madam,” Tessa looks at Y/N with pity in her eyes. She must have heard the whole conversation. 

She follows Tessa and locks herself into the bathroom, which is bigger than her fucking apartment it seems. 

After a while of watching youtube videos, she walks out and crosses the entrance section. She can hear that there’s a heated argument going on in the dining room.

“Always make fucking sure to protect your assets! I thought you had a fucking brain!” It’s John’s voice. 

“Stop it, dad!”

“Damn, son! I thought you would be better prepared so not let some girl screw you over!”

“I don’t have a prenup because we are not fucking married, alright? It’s just for fucking show!” Dean’s so loud, it makes her jump and his words hurt, it really does. He’s not wrong but they hurt nonetheless.

“What do you mean it’s fake?” It’s now Mary who asks the question.

“It’s as fake as it can get. I am being blackmailed and I have to pretend to be married to Y/N to get the other girl off my fucking back!”

She hears Mary gasps, “Oh, thank god,” And then his mother adds, “I thought it was real how you gushed over her. I’m so glad it’s fake,”

“Mom—” 

Y/N’s heard enough. 

She walks straight to the door. She wants to be quiet, but the door’s heavy and it closes with a bang. She’s halfway to the car when Dean flies out, calling after her.

Damn his fucking long legs. He’s grabbing at her to turn her around and she can’t hide it. Can't hide the tears that are running down her cheeks. 

“Where do you think you’re going?”

“Home,” She says, but she doesn’t look him in the eyes, “My home.” 

Y/N’s angry, but she can’t quite tell him why. She can’t tell him that hearing him telling his parents that what they have is fake, hurts her because he’s actually not wrong. It’s the fucking truth and if she has a problem with it, it’s her own fucking problem. It’s not her place to be angry because everything is indeed fucking fake! 

She shakes him off and Gabe opens the door for her to get in. “I need space, Dean. Give me that. Make some excuse for me.” 

She expected him to lash out, to be angry at her and demand of her to hold on to the contract and make her stay, but he doesn’t. He steps back and nods, “I understand,” He turns to Gabe, “Drive her home safely and come back,”

With that, he closes the door and lets her drive a way. Gabe didn't talk the whole way which she’s glad about. 

Before she gets out, she takes off her rings, figuring things were over anyway, and hands them to Gabe.


	20. CH20 (FIN)

Y/N wakes up to the sound of her alarm. It takes her way too long to realize where she is. 

She opens her eyes and takes a look around. Her room kind of looks small compared to the room she called her own in Dean’s apartment.

Today is Monday, which means that she’s supposed to go to work and she kind of doesn't want to. She hasn’t heard from Dean. He didn’t text her, nor did he call. Maybe it’s over before it’s over. Maybe today, he’ll say that she can get out if she wants. He and Sam have the evidence and they can build up their case around it. There’s really no need for him to fake it with her anymore.

Yesterday she had to go out and buy clothes because all her stuff is still at Dean’s, and she didn’t want to go there. She spent the rest of the day in her bed, buried in her novels. It would have been relaxing if she hadn’t thought about Dean so much.

She’s so nervous about meeting him again that she has had an awful night’s sleep. She’s nervous, when it should be easy. He’s her boss. She’s his employee. It should have always stayed like that, she realized. She should have never let them talk her into crossing the line. 

Her anxiety peaks as she takes the subway to the office. She feels nauseous. It doesn’t help knowing that her period is a little late too. She hopes that she’s not pregnant. She’s been taking her pills regularly. It shouldn’t be a problem and honestly, she doesn’t need to add it to her pile of worries. 

Arriving in the office, she sees that Ruby’s already there but it’s awfully quiet. She sits down and starts her computer. 

“Psssst,” Y/N hisses at Ruby who’s engrossed in a paper.

“Oh, hey! How was meeting with the parents?” Ruby grins.

“Sam didn’t tell you anything?” She frowns, wondering why Dean hasn’t updated Sam on what happened. On how she walked out of there and left him behind to hole herself up in her own apartment. 

Ruby shrugs, “No?”

“Ruby, I’m late.” She says, because she wants to get that off her chest first. 

Her friend raises her eyebrows and she sees that Ruby’s eyes travel to the clock, “I’d say your early, Dean’s not even in yet.” 

“No, I’m late!” She hisses, her eyes widen as she tries to get Ruby to understand. 

Ruby’s mouth forms an ‘O’, “Ooooh, shit.”

“Yeah,” She sighs. 

“How many days?”

“Three.”

“That’s nothing, right? Maybe it’s the stress? You’re under a lot of pressure.” 

Y/N knows that Ruby’s just trying to cheer her up, “Yeah, maybe.” She says and types in her password.

“Lets work, alright, we can think about it on our break. I can go get a test for you. Now, I want you to distract yourself with work or else you’ll go mad.”

“Yeah, okay,,” She tries to smile at her friend. The last thing she wants is for Ruby to be worried about her and Ruby’s not wrong. If she throws herself into work, it’ll definitely help distract her mind from all of the things that’s making it hard for her to breathe.

When her computer starts up her email box begins to fill itself. She sees that she has an unusually high amount of emails. Half of them are from Dean. Sent during their fake honeymoon. She wonders why, as they were practically together all the time? 

She opens up the first email.

 **Saturday, [00:24AM]:** I’m sorry that I’ve upset you.

 **Saturday, [01:12AM]:** Do you think I’m crazy when I tell you that I can’t fall asleep without you next to me?

 **Saturday, [05:21AM]:** You’re the cutest crankiest person I ever laid eyes on.

 **Saturday, [08:31AM]:** You fell asleep right after take off. I’ve taken a picture of you. Sorry not sorry. 

**Saturday, [09:23AM]:** You’re sleeping again. You really do need a lot of sleep, don’t you? Or maybe it’s because you’re too nervous of flying. I’m sorry I didn’t even ask if flying would be okay for you. I never took it into consideration that you might not like flying. The thought had never crossed my mind. I’m trying to help you through it, though.

 **Saturday, [11:42AM]:** You’re cute when you’re all giddy about being here and I’m happy that you let me bring you here. Can’t wait until I can show you our room. I have a feeling that you’ll like it.

 **Saturday, [01:12PM]:** You didn’t need to ask if you can take a dip in the sea but you still did. That’s what I like about you. You don’t take anything for granted. 

**Saturday, [02:57PM]:** For god’s sake, you fell asleep on the lounger. You’re going to get sunburned!

 **Saturday, [04:32PM]:** You’re still distracting me. But I kind of like it. Maybe I’m a closet masochist.

 **Saturday, [09:22PM]:** You know what I absolutely love? I fucking love how you taste, how you want me to fuck you harder. How wet you are for me. I love how you look when you’re laying on the bed, spit slick and pink all over.

 **Saturday, [11:46PM]:** Jesus, you’re laying there, pink pussy in full view. You have no idea what you’re doing to me.

Tears start to pool in her eyes but there’s more. 

*

**Sunday, [11:21AM]:** It was nice waking up to you beside me. I can get used to it. Would love for it to happen every morning.

 **Sunday, [03:42PM]:** You really love snorkeling, don’t you? Don’t even want to get out of that water. You’ll be sunburned if you’re not careful, baby.

 **Sunday, [08:23PM]:** You fell asleep before room service arrived. I had to take a picture. I don’t think you know how much you affect me.

*

**Monday, [03:12AM]** : I woke up thinking you’re not here, but you are. 

**Monday, [09:34AM]:** You locked yourself in the bathroom because I woke you up. Definitely the crankiest person ever. Wonder why you think that I’m the grumpy one here.

 **Monday, [02:22PM]:** I’m working inside and you’re distracting me again. Stretching yourself half naked on the lounger. It’s not really fair. 

**Monday, [11:43PM]:** Would you think I’m crazy when I tell you that I have fallen for you? Because I think I have. More so than I already had.

Yeah, those are definitely tears that streak down her face. She tries not to make it obvious to Ruby but she has her nose buried in the paper, so she should be good.

*

**Tuesday, [11:43AM]:** You woke me up with a smile. I’m the happiest when I get to be inside you. I urged you to send a picture to Ruby. But in reality, I want her and Sam to see it too. Little do you know that I already have many pictures of you in my phone. By the way, I love how you get wetter when I talk dirty to you.

 **Tuesday, [12:01PM]:** I think I might love you. 

**Tuesday, [01:59PM]:** Gearing up for my conference call but all I can think about is you in the pool.

 **Tuesday, [03:44PM]:** I’m hearing your moans while you get massaged. This is torture.

 **Tuesday, [05:02PM]:** I can’t stop myself from showering you with affection. I hope you don’t mind.

 **Tuesday, [07:23PM]:** Waiting for you to come out of the bathroom. You take your sweet time but I don’t really care about it anyway. I’m sure you look stunning whatever you wear or put on your face. Prettiest thing if I ever did see one. I don’t know how I can make you understand that this is real. This is all me, and all of me wants all of you.

*

**Wednesday, [02:11AM]:** You looked absolutely stunning tonight. I’m sorry that she pulled your brother into this. That was never my intention. I was never going to hurt you or your family and I’m doing my best to help you protect him. And I try my best to protect you, too. You know, you managed to calm me down. I don’t know how you did that, but you did. I remember hearing your faint voice in my rage. And when I turned around, it’s only you that I saw. I told you that you’ll be able to go back to your old life soon. That’s true. I don’t want you to think that you can’t. I’d just prefer if you’d stay, but that’s not on me to decide. 

**Wednesday, [03:02AM]:** Yeah, it’s definitely love.

 **Wednesday, [05:34AM]:** I’m up because I’m partly nervous about meeting your brother.

 **Wednesday, [10:27AM]:** You looked so peaceful in your sleep. I might have taken another picture. You asked if we can stay in bed a little longer and honestly, all I wanted in that moment was to cancel everyone and stay in bed with you.

 **Wednesday, [03:11PM]:** On my way to go fishing with Jack. He’s a great guy. I like him a lot. He reminds me of you. 

**Wednesday, [07:18PM]:** We’re back. We talked things through. He’s very protective of you. We both are. He knows how I feel for you. That’s all I want him to know. I want him to work at the company, he’s more than qualified.

 **Wednesday, [11:18PM]:** Currently waiting for you to wash your face and come to bed. I love seeing you happy. It literally makes my day. Some might call it love. I think I do too.

*

**Thursday, [02:24AM]:** Can you tell why I’m always waking up in the middle of the night? Mostly it’s because I have to make sure that you’re still here. I meant it when I said that Jack could live with me. I hope that by that time you’ll still be living with me too. I’d love that, because I love you.

 **Thursday, [05:52AM]:** I don’t know how I should feel about the new development. It means that what we have will be over soon, doesn’t it? What if I don’t want it to be over? Would you be game?

 **Thursday, [06:31AM]:** I’ve made a decision. I want to keep you a little longer. Even if it’s only for two weeks. I know that I told you that you can go back into your old life. It’s because I’m a coward and can’t tell you the truth. If I had my way, I’d keep you forever but you make your own decisions.

 **Thursday, [10:34AM]:** I lied about getting back and building a case. It’s only partly true. I want to take you to my parents, I want them to understand that there’s nothing fake about what we have. I want them to get off my case so I have one less thing to worry about. I’m sorry if that sounds selfish.

She has to pause to blow her nose. Ruby still doesn’t notice that she’s sobbing, because she’s on the phone now.

*

**Friday, [04:21AM]:** You’re still here. Thank god.

 **Friday, [04:21AM]:** I love you.

 **Friday, [02:11PM]:** I watch you splash around with Jack and Ruby. I can get used to seeing your genuine smile more often. I want you to be happy. You deserve everything good in your life.

 **Friday, [06:44PM]:** You’re getting ready in the bathroom. I’m sad we’re going home tomorrow. I want you. I want you so fucking bad. 

*

**Saturday, [03:03AM]:** We’ve made love but I’m up and I want more. I want to stay inside of you. I want to show you how much I love you.

 **Saturday, [07:10AM]:** The alarm has already gone off twice. I couldn’t bring myself to wake you up. I don’t even care if we’ll be late. It’s good like this. Waking up with you in my arms.

 **Saturday, [10:32AM]:** You’re talking with Jack. I like that. I like to see you happy. Like to see him happy. It literally makes me happy seeing how you two treat each other. Jack knows that I only want the best for you. I hope he doesn’t tell you what we talked about, though. Because we would both have to kill you if one of us does.

*

**Sunday, [02:01AM]:** That backfired, didn’t it? You left and I didn’t hold you back. Not because I don’t want to. It’s because I don’t want you to think that I haven’t given you any options. I don’t want you to think that you’re not allowed to walk away, even when we have a contract. I want you to know that you can get out any time you want. I don’t care about the Amara case anymore. All I care about is for you to be happy. 

**Sunday, [04:33AM]:** I can’t sleep. You’re not here.

 **Sunday, [10:28AM]:** I don’t want you to think that me not calling you is because I don’t care. I do. But I want to give you the space you need, even if it kills me.

 **Sunday, [08:47PM]:** It’s weird around here without you.

*

**Monday, [03:49AM]:** I’m still awake because I don’t know if I should go into work. You probably don’t want to see me, so I’m taking the day off. Don’t worry about me. I’ll see you on Tuesday.

 **Monday, [03:51AM]:** If you see your emails when you get to work, you’ll probably think that I’m crazy. It’s just… I’m not really good at expressing my feelings, and it’s especially hard when it comes to you. I get tongue tied and my heart does somersaults. I know that it’s unlike my work persona but that’s just how I am. That’s why I’m sending you emails, hoping that I can get you to understand how much you actually mean to me.

 **Monday, [04:00AM]:** I wish you were here.

 **Monday, [04:01AM]:** I love you.

Y/N’s full on wailing and even Ruby notices it now, how can she not?

“Babe, are you okay?” Her friend stands up and walks over to her, sees her screen with all the opened emails and reads some of them, “Oh my god, the boss is such a fucking sap!” They both have to chuckle.

Y/N fishes her phone out of her purse and thumbs over a number, “Tell me what he told you, Jack. I need to know!”

Her brother sighs on the other side, “Fine, but don’t tell him I told you!”

“I won’t,”

“He made sure that I understood his feelings for you. That it was never a fake marriage to him. He was just too nervous to ask you out and when that thing with Amara happened, he saw it as an opportunity to do the right thing. He’s thinking about marrying you for real if you want that in your future. But I told him that he had to get my blessings first — which I gave him by the end of the finishing trip.”

“Jack!”

“I’m sorry. He’s good, Y/N. You know how I’m always overprotective and I was with Dean, too. But his intentions are good. He told me how you met. He knows every little detail. He could even tell me what you wore that day. Dean knows more about you than you think he does. Hell, he knows more about you than I do!”

“Well, then he’s a stalker.” She scoffs.

“Y/N, you wouldn’t know what’s good if it hit you in your face.”

“Did you talk to Ruby?”

Jack laughs, “I don’t have to talk to Ruby to know that about you.”

“Okay, thanks, Jack.”

“Anytime, sis. I love you.”

“I love you, too.”

She hangs up and stands up from her chair to look at her friend, “Ruby?”

“Yeah, I can manage here. Go get him!”

  
  
  


*

  
  


Dean’s on the terrace, his hands on the railing. He’s already dressed in trousers and a button up shirt even though he has taken the day off. Old habits apparently die hard.

She slides the door open quietly.

“I was wondering if you’d show up,” He says and he turns around, rests his lower back against the railing. He’s not smiling.

Y/N walks closer, takes off her suit jacket and leaves it on the ground, feeling hot from running here. She already took off her shoes by the door. She’s sure that she’ll have blisters tomorrow. 

His eyes are on her as he watches her clutching the railing next to him. She’s looking out when he’s looking towards his penthouse.

“How could I not?” She says after a long while and she hears him exhale. 

“You’ve seen the emails.”

She nods, “I have,”

Dean turns around and moves behind her, places his hands on either side of hers and presses his body closer, caging her in. She feels him lowering his face, feels his lips on her throat. He kisses her and leaves them there. Her heart’s almost exploding.

“I don’t know how much you’ve heard before you left,” He’s talking about the dinner at his parents' place, she knows, “If you’d have stayed and listened longer, you would have heard me telling them that even though it’s fake, it feels fucking real to me. You would have heard me telling them that I wanted to ask you out properly and they would have to accept that I want you. That we were going to get an annulment and maybe one day I’ll get to pop the real question,”

“Would you want that?” 

He chuckles, “More than you know. I’d love for you to come back and spend the next two weeks here until this is all over. And after that, I’d love for you to stay. But also I’m not holding you back. If you want out, I’m gonna tell Sam to release you out of the contract.”

She turns in his grip and wraps her arms around his waist, places her cheek on his chest. Dean’s heart is beating as fast as hers.

After a while, she looks up at him, stands on her tip toes and kisses his cheek. 

“I hope that means that you’re coming back,” He smirks at her. 

“You want me to come back.”

“I’m lonely when you’re not here. I want you to move in, for good, if you want. Come on, tell me what it takes for me to get you to come back.”

She thinks about it. It would be too soon to move in with him and right into his room, no? She raises her eyebrows, “I still want my own room.” 

“It’s yours. You can have all the rooms you want.Maybe you want a room for your novels?” He’s laughing and she punches his chest.

Y/N gnaws on her bottom lip, “I want to take Fridays off occasionally because I want to see Jack more often,”

He purses his lips into a thin line and grins, “Granted,”

She looks at him, squints her eyes.

Dean chuckles, “Come on, what else? We’re negotiating. I like that,”

“Okay, when I say I want my space, you gotta give me that,”

“Of course,”

“No making fun of my books.” She’s pouting.

“I would never. At least not anymore.”

She looks at him to see him holding in a laugh.

“I don’t want you to treat me different to the other employees,”

Dean frowns, “You contradict yourself, because you basically just asked me for Fridays off.”

“That’s different,” She grins and he throws his head back to laugh, and she adds, “I don’t want you to wait for me every morning, because I don’t want to start as early as you do.”

“That, I can do. Try to be quiet so as not to wake up cranky — got it.” He winks, which earns him another punch to the chest.

“I might be pregnant,” She drops it like it’s fucking hot and Dean’s smile disappears. She goes on before he can utter a word, “And I know that you don’t want kids so I don’t even know what to think of it.”

Dean’s brow meets in the middle of his forehead, “Who said that I don’t want kids?”

“You? When you were telling it to Chuck and Naomi to excuse my outburst.”

He breathes out a weak smile, “That was just that, an excuse,” He kisses her forehead, “I would take full responsibility if you are. Maybe I’m hoping that you really are? Would it be bad?” 

“Well, yeah? I’m not ready yet.” She gestures wildly with her hands.

Dean pecks her lips, smiling before he digs around in his pants, goes down to his knees and she’s full on frowning.

“Do you wanna marry me, for real?” 

“No, Dean,” She says but she smiles, “I don’t want that. At least not yet.”

If Dean’s surprised by her saying no to him, he doesn’t let on. He stands up, takes her hand and slips the rings back onto her finger anyway because they’re still pretending for the next two weeks. His arms come around her and she hugs him in return, pressing the side of her face against his chest, listens to the staccato beat of his heart, “I won’t stop asking, though. You know I can be persistent.”

Oh yeah, she knows that. She buries her face into his shirt, breathes in his scent and mumbles, “Why do you want to marry me for real?” She has to ask. She’s too curious now.

“Because,” Dean holds her a little tighter, kisses the crown of her head, “You deserve good things and I wanna be one of them.”

She chuckles, “Jack told me what you talked about.”

“And he didn’t kill you?” Dean squints his eyes at her. He looks comical, it makes her smile, and then he adds, “That’s not what we agreed on, dammit, Jack!”

Dean’s laughing and she punches his chest, “Is it true that you know every detail of how we met?”

“Yeah,” He moves to kiss her forehead when she looks up, “When I told the reporters on our first social outing that I fell for you the moment you bumped into me, and I told you later that I fell for you when you smiled at me? That’s all true. It took me a week to go into that damn coffee shop, always backed out before I got to the door so many times. And then, when I finally found the courage and stepped in, you greeted me with a smile. However, the smile disappeared when you saw that it was me.”

She grins at the memories, “I was scared that you want me to pay for your ruined suit. I don’t have that kind of money,”

He chuckles, “That’s okay. I was going to ask you out then, but I chickened out. So instead, I offered you a job, thinking that if I’m too nervous to ask you out, maybe I can have you close and see you every day. Your smile is addictive. I thought that I was going to work on my courage in asking you out. Or maybe I thought that seeing you every day might put me off, maybe I thought that I’d see a side of you I don’t like, but that never happened. I liked every fucking thing about you. It had been a year and I still hadn’t asked you out.”

Dean lowers his forehead to her shoulders and her hand goes up to stroke his head.

“You’re so good with words, how come you couldn’t?”

“Because,” He looks up again, kisses her, “I had such a huge crush on you, and every time I was around you, I was angry at myself for not being able to ask you out.”

“‘S that's why you were so grumpy all the time?”

He lets out a huff of air, “Yeah,”

“You’re the worst,” She smiles.

“I know,” Dean says, “But I’m much more confident now,” He kisses her again. His lips feel familiar on her own, “What do you say. Reckon you can skip work for the day? I’m taking you on a date, I heard you like aquariums?”

Y/N really does. How does he even know?

Frowning, she looks at him, “I don’t know, my boss can be a dick sometimes. He probably won't give me the day off.”

Dean grins, licks his lips before they curve into a big and wide smile, he kisses her forehead, her nose, her lips, “Baby, I’d give you the world.”

_**~~T H E E N D~~** _


	21. Epilogue

**Notes for the Chapter:**

> So, we've reached the end of the road. I hope you had fun reading it as much as I had fun writing it :)

She had moved back on the same day, and into his bed that same night. She still kept her room but Dean was okay with that. She mostly sleeps there when he comes home late. Dean would then go in and take her back into his bed. He has perfected his techniques and now she doesn’t even stir when he scoops her up and carries her back into his bed. Their bed. 

It’s true that she kept the room as hers but she had moved all her clothes into his room by the time they annulled their marriage. 

It was never an option for her to stop working for him. But she stayed as his PA and they hired someone else to help with Ruby’s load of work. Their relationship had never been questioned by his staff. Dean thinks that he can count himself lucky for having great and loyal employees. He got his temper under control, too. He only fired one person in the last three months which is a huge improvement.

The marriage with Amara was a piece of cake. After Amara got wind of the existence of the tape, she was quick to agree for the annulment and Dean could even get money out of her. Serves her right, really. He used the money to give his employees a big bonus. 

They have gotten over the initial pregnancy scare too. Turned out that she was indeed just stressed. He was a little disappointed, couldn’t lie about it, but she was happy so there’s that. He’d like to have kids one day, and especially with her. Dean knows that she wants kids too, but not right now. He hopes that she wants kids with him, though. 

Dean really didn’t give up on asking her to be his real wife. He would drop it in the weirdest times. It’s a game he plays and he actually enjoys it. He has gotten her another ring. Doesn’t want to ask her with the same ring they already sealed their fake marriage with, it just didn’t seem right.

  
  


*

  
  


The first time he popped the question was after they were fake husband and wife and only girlfriend and boyfriend. She was sitting in the tub when he came back from work because he still worked longer than she did. Dean peeled himself out of his clothes to join her, “Do you wanna marry me?” He’d asked before he sits in the tub and grabs her by her arm to place her onto his lap.

“No,” She giggled and he buried his face into the crook of her neck, sucked at her skin until she moaned a  _ yes _ but it’s not the answer, he knew.

  
  


*

  
  


The fourth time he asked her to be his wife, Y/N was lying on the couch when he walked in after a long working day. She was reading a book and she was wearing one of his shirts and only panties and that did things to him. Especially when half her ass cheeks poked out of it. He looked and smirked before he walked over to the drawer with food delivery leaflets. He held the leaflets in his hand and looked over to her before he asked, “Do you want to marry me or shall we order in food?”

Laughing, she said no, and that she wanted pizza with pineapples.

  
  


*

  
  


The ninth time Dean asked her was at work. He came out of a meeting and walked past her desk, dropping off his notes for her to put down on paper. She was so lost in her work that she didn’t even notice him standing next to her, so he lowered himself with one hand braced on her chair and whispered into her ear, “Do you want to marry me?”

She rolled her eyes but she kissed his cheek. It was enough fuel to get into the next meeting. 

  
  


*

  
  


The twelfth time he asked her was when she was laying between his thighs and he had spread them for her to be able to reach his rim. He was there, held up his legs by the back of his knees and looked down. He would have loved to take a picture if his hand were free. 

His balls are heavy on her nose, his dick, hard and leaking, was resting over half her face. It was a sight to behold, and in that moment his heart felt so full so he whispered, “Do you want to marry me?”

She ignored him and continued licking at his rim and sucked in his balls that made him choke on his own words.

  
  


*

  
  


The seventeenth time that he popped the question was while they were in a meeting together. They listened to Garth's new idea on office improvements and she was typing away on her laptop when he sent her an email, “Please be my wife?”

Y/N frowned, her lips pulled into a thin straight line before she clicked on her mouse and soon his phone vibrated. Dean took it out and thumbs over her email of Michael Scott from  _ The Office _ screaming  _ No _ meme.

  
  


*

  
  


The twenty-third time Dean had asked her, they were having dinner with Jack and he had told the waiter to put the ring in her glass. What Dean hadn’t accounted for, was that the waiter would be so dumb and mix up their glasses. So when Jack drank his champagne he had the ring in his mouth, and damn near choked on it. Y/N had stomach cramps from laughing too hard.

But hey, Jack said yes and they’re planning a spring wedding. 

Jack is a great guy. Dean’s glad that he took Jack on a fishing trip back in Jamaica. Jack was so hostile towards him and Dean just knew that he had to pour his heart out to Jack to get him to understand that he was never just in it for the fake marriage. It meant so much more to him. Thinking back, it needed a lot of courage from Dean to do so. Jack didn’t speak for an agonizing long time and it was while they were on the boat and Dean had almost gotten sea sick than he started to speak the truth. 

Jack smirked when he saw that the blood had drained from Dean’s face.

“Do you like fishing?” Jack had asked him.

“Yeah but from the shore.” Dean answered, trying not do fucking puke. 

Jack laughed at him but apparently, the trip had helped cement their friendship.

  
  


*

  
  


The twenty-ninth time he asked was when he ate her out and she moaned  _ yes yes  _ above him. He paused and mumbled against her wet cunt, “You wanna marry me?”

She came right on the spot but not without moaning out something that sounded awfully like  _ fuck no _ .

  
  


*

  
  


The thirty-third time Dean asked, was when they spent a weekend away at a secluded cabin in Colorado. 

That’s another thing that Dean loves about her. When things get too stressful, she always made sure that he took a break and she planned trips that should take his mind off work. She feared that he’ll overwork himself, which is not entirely wrong.

So when they were roasting marshmallows over a fire, he wrapped his arm around her, and asked her if she wanted to be his wife. 

She didn’t answer, instead she said, “You’re not going to give up, do you?” 

He smiled down and kissed her forehead, “Nope.”

  
  


*

  
  


The thirty-eight time Dean popped the question was during a game night of pictionary with Sam and Ruby and her brother. Yeah that’s right, Sam never let Ruby go again. Dean swears, if they marry before him...

Dean drew a ring onto the board with a question mark and instead of answering right, she just said “ _ Lord of the Rings?” _

Even Jack grew a little annoyed at her and screamed that she should _fucking say_ _yes already_.

  
  


*

  
  


The forty-fifth time he asked, they were at a concert and she stood before him, his hands around her waist as she leaned her head against his chest. He placed a kiss on the crown of her head, “Do you want to marry me?”

The one girl next to them gasped loudly and she pushed her boyfriend out of the way, thinking that Dean needed room to go on his knees. They had to laugh and explain that his girlfriend is not saying yes, so there’s no worry. The woman was embarrassed and Dean took Y/N’s hand to move further back. 

  
  


*

  
  


The fifty-second time Dean asked, was when he came home from a work trip. It didn’t go very well so he was kind of down. He found her in the guest bedroom, sleeping on her side and Dean scooped her up, carried her into their bed and left to take a shower. 

When he came back, she was partially awake. And it’s like she knew because she opened her arms for him to crawl in. He placed his head on her chest, letting her stroke his head. 

“Please be my wife?” He’d asked, but there’s no answer. Her heart beat slow, she was already asleep.

  
  


*

  
  


The fifty-third time he asked, was the next day right after the fifty-second time. Dean spooned her from behind, rained kisses onto her shoulder and neck, she stirred awake, “I really wish you’d say yes.”

It was not really a question. Just a statement.

“Okay,” She said and Dean’s heart picked up speed.

“Okay?” He asked again, just to be sure.

“Yes,” She turned around in his grip and cradled his face between the palms of her hand, “I’m saying yes,” 

Dean kissed her while smiled like a fucking idiot, held her tighter, “Fucking finally,” he mumbles against her lips.

  
  
  


***

  
  


They married in a small ceremony with just the closest of people and no press, because he still took her out to social events and they all thought she was his wife anyway. It’s easier that way. It feels more real. 

Sam and Jack were both his best men while Ruby resumed her position as a bridesmaid. 

Dean didn’t make a prenup; it's his way to piss off his parents. It’s the right decision, he thinks. Y/N never once asked him for money. She hates being dependent on him and sometimes there were petty fights when she wouldn’t allow him to buy her something. However, she let him pay for Jack’s tuition and that is progress. 

Like Dean said before, he would give her the world and so much more but she’s happy as it is and that’s the most important thing actually, because he’s happy too when she’s happy. He’s less grumpy, less hot headed and, that’s not a lie nor an exaggeration, he’s the happiest he’s ever been.


End file.
